1438-16-0

Basic information

• Product Name: N-Aminorhodanine
• Synonyms: TIMTEC-BB SBB000101;N-AMINORHODANINE;3-Amino-2-thioxo-1,3-thiazolidin-4-one;3-amino-2-thioxo-4-thiazolidinon;4-Thiazolidinone, 3-amino-2-thioxo-;AKOS B028622;3-AMINO-2-THIOXO-THIAZOLIDIN-4-ONE;3-AMINO-2-THIOXO-4-THIAZOLIDINONE
• CAS NO: 1438-16-0
• Molecular Formula: C₃H₄N₂OS₂
• Molecular Weight: 148.21
• EINECS: 215-870-9
• Product Categories: Miscellaneous;Building Blocks;Heterocyclic Building Blocks;Thiazoles
• Mol File: 1438-16-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 100-103 °C(lit.)
• Boiling Point: 268.2 °C at 760 mmHg
• Flash Point: 116 °C
• Appearance: /solid
• Density: 1.455 (estimate)
• Vapor Pressure: 0.0078mmHg at 25°C
• Refractive Index: 1.7000 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: -2.30±0.20(Predicted)
• CAS DataBase Reference: N-Aminorhodanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Aminorhodanine(1438-16-0)
• EPA Substance Registry System: N-Aminorhodanine(1438-16-0)

Safety Data

• Hazard Codes: T+
• Statements: 24-28
• Safety Statements: 22-28-36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: XJ6183750
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 1438-16-0(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

InChI:InChI=1/C3H4N2OS2/c4-5-2(6)1-8-3(5)7/h1,4H2

Synthetic route

bis(carboxymethyl)trithiocarbonate (6326-83-6) → 3-aminorhodanine (1438-16-0)

Conditions	Yield
With water; sodium carbonate; hydrazinium sulfate

dithiocarbonic acid hydrazide (471-32-9) + chloroacetic acid ethyl ester (105-39-5) → 3-aminorhodanine (1438-16-0)

Conditions	Yield
Umsetzung des Reaktionsprodukts;

dithiocarbonic acid hydrazide, hydrazonium salt (20469-71-0) + chloroacetic acid (79-11-8) → 3-aminorhodanine (1438-16-0)

Conditions	Yield
In water

chloroacetic acid ethyl ester (105-39-5) + dithiocarbazinate of hydrazine → 3-aminorhodanine (1438-16-0)

Conditions	Yield
With ethanol

sodium monochloroacetic acid (3926-62-3) + hydrazine salt of/the/ dithiocarbazic acid → 3-aminorhodanine (1438-16-0)

Conditions	Yield
With water anschliessendes Behandeln mit wss. HCl;

sodium monochloroacetic acid (3926-62-3) + potassium-salt of/the/ dithiocarbazic acid → 3-aminorhodanine (1438-16-0)

Conditions	Yield
With water anschliessendes Behandeln mit wss. HCl;

dithiocarbonic acid hydrazide (471-32-9) + water (7732-18-5) + sodium monochloroacetic acid (3926-62-3) → 3-aminorhodanine (1438-16-0)

Conditions	Yield
Reaktion des Kalium-Salzes oder des Hydrazinium-Salzes; anschliessenden Behandeln mit wss.Salzsaeure;

3-[2-Methyl-prop-(E)-ylideneamino]-2-thioxo-thiazolidin-4-one → 3-aminorhodanine (1438-16-0) + isobutyraldehyde (78-84-2)

Conditions	Yield
In phosphate buffer; water-d2 pH=7; Equilibrium constant;

4-{[(E)-4-Oxo-2-thioxo-thiazolidin-3-ylimino]-methyl}-benzoic acid → 3-aminorhodanine (1438-16-0) + 4-Carboxybenzaldehyde (619-66-9)

Conditions	Yield
In phosphate buffer; water-d2 pH=7; Equilibrium constant;

3-aminorhodanine (1438-16-0) + 4-methoxy-benzoyl chloride (100-07-2) → 4-methoxy-N-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzamide (82220-84-6)

Conditions	Yield
In benzene for 3h; Heating;	96%

3-aminorhodanine (1438-16-0) + 4-tert-Butyl-2-methylsulfanyl-3-(3-trifluormethylphenyl)thiazoliumiodid → 3-Amino-5-[4-tert-butyl-3-(3-trifluormethylphenyl)-2,3-dihydrothiazol-2-yliden]-2-thioxothiazolidin-4-on

Conditions	Yield
With lead(II) nitrate; triethylamine In dichloromethane for 1h; Condensation; Heating;	96%

3-aminorhodanine (1438-16-0) + 4-hydroxy-3,5-diiodobenzaldehyde (1948-40-9) → (Z)-3-amino-5-(3',5'-diiodo-4'-hydroxybenzylidene)-2-thioxothiazolidin-4-one (1133953-95-3)

Conditions	Yield
With acetic acid; triethylamine In ethyl acetate at 85℃; for 3h;	96%

3-aminorhodanine (1438-16-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → ethyl (5-oxo-2-thioxo-[1,3,4]thiadiazinan-6-ylidene)acetate

Conditions	Yield
With triphenylphosphine In dichloromethane at 20℃; for 2h;	95%

3-aminorhodanine (1438-16-0) + Ethyl oxalyl chloride (4755-77-5) → N-(4-oxo-2-thioxothiazolidin-3-yl)oxalamate (1449039-21-7)

Conditions	Yield
With triethylamine In ethanol at 20℃; for 1h;	95%

3-aminorhodanine (1438-16-0) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3-{[(3,4-dimethoxyphenyl)methylene]amino}-2-thioxo-1,3-thiazolidin-4-one (19745-79-0)

Conditions	Yield
In ethanol at 20℃; for 5h;	94%
In ethanol

3-aminorhodanine (1438-16-0) + 3-phenyl-propenal (104-55-2) → 3-{[(2E)-3-phenylprop-2-en-1-ylidene]amino}-2-thioxo-1,3-thiazolidin-4-one (52514-13-3)

Conditions	Yield
In ethanol at 20℃; for 5h;	92%

3-aminorhodanine (1438-16-0) + 1-methyl-5-nitro-1H-indole-2,3-dione (3484-32-0) → (Z)-3-amino-5-(1-methyl-5-nitro-2-oxoindolin-3-ylidene)-2-thioxothiazolidin-4-one

Conditions	Yield
With acetic acid In ethanol at 100℃; for 0.0833333h; Knoevenagel Condensation; Microwave irradiation;	92%

6-methyl-2-pyridinecarboxaldehyde (1122-72-1) + 3-aminorhodanine (1438-16-0) → 3-Amino-5-[1-(6-methyl-pyridin-2-yl)-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one

Conditions	Yield
With piperidine In ethanol for 3h; Heating;	91%

3-aminorhodanine (1438-16-0) + 4-nitro-benzoyl chloride (122-04-3) → 4-nitro-benzoic acid-(4-oxo-2-thioxo-thiazolidin-3-ylamide) (82220-83-5)

Conditions	Yield
In benzene for 3h; Heating;	90%
With benzene

3-aminorhodanine (1438-16-0) + Di-tert-butyl acetylenedicarboxylate (66086-33-7) → tert-butyl (5-oxo-2-thioxo-[1,3,4]thiadiazinan-6-ylidene)acetate

Conditions	Yield
With triphenylphosphine In dichloromethane at 20℃; for 2h;	90%

3-aminorhodanine (1438-16-0) + dimethyl acetylenedicarboxylate (762-42-5) → methyl (5-oxo-2-thioxo-[1,3,4]thiadiazinan-6-ylidene)acetate

Conditions	Yield
With triphenylphosphine In dichloromethane at 20℃; for 2h;	89%

3-aminorhodanine (1438-16-0) + 4-cyanobenzylidenemalononitrile (36937-92-5) + 4-thioxodihydro-2,6(1H,5H)-pyrimidinedione (15998-99-9) → 7-amino-5-(4-cyanophenyl)-1,2,3,4,5,8-hexahydro-2-oxo-8-(4-oxo-2-thioxothiazolidinyl)-4-thioxopyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With nano-SPIA In ethanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide for 1.5h; Reflux;	88%

3-aminorhodanine (1438-16-0) + 1,2-diamino-benzene (95-54-5) → Benzimidazol-2-thiol (134469-07-1)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene Heating;	87%

3-aminorhodanine (1438-16-0) + (E)-3-(((1H-indol-3-yl)methylene)amino)-2-thioxothiazolidin-4-one → (Z)-5-((1H-indol-3-yl)methylene)-3-(((E)-(1H-indol-3-yl)methylene)amino)-2-thioxo thiazolidin-4-one

Conditions	Yield
In ethanol for 8h; Reflux;	87%

glutaric anhydride, (108-55-4) + 3-aminorhodanine (1438-16-0) → 1-(4-Oxo-2-thioxo-thiazolidin-3-yl)-piperidine-2,6-dione (182558-47-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Heating;	86%

3-aminorhodanine (1438-16-0) + 7-diethylaminocoumarine-3-aldehyde (57597-64-5) → (3-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)amino)-2-thioxothiazolidin-4-one

Conditions	Yield
In acetonitrile at 20℃; for 3h;	86%

3-aminorhodanine (1438-16-0) + indole-2,3-dione (91-56-5) → (E)-3-amino-5-(2-oxoindolin-3-ylidene)-2-thioxothiazolidin-4-one

Conditions	Yield
With ammonium chloride In ethanol at 100℃; for 5.16667h;	86%

3-aminorhodanine (1438-16-0) + 3-nitro-benzaldehyde (99-61-6) → 3-(3-nitrobenzylideneamino)-2-thioxothiazolidin-4-one (17521-18-5)

Conditions	Yield
With aluminum oxide for 0.0944444h; Microwave irradiation; Neat (no solvent);	85%
In ethanol

succinic acid anhydride (108-30-5) + 3-aminorhodanine (1438-16-0) → 3-(2,5-dioxopyrrolidin-1-yl)-2-thioxothiazolidin-4-one (182558-46-9)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Heating;	85%

methanol (67-56-1) + 3-aminorhodanine (1438-16-0) + 3-nitro-benzaldehyde (99-61-6) → methoxycarbonylmethyl 3-(3-nitrobenzylidene)dithiocarbazate

Conditions	Yield
With hydrogenchloride In water for 8h; Reflux;	85%

3-aminorhodanine (1438-16-0) + 5-fluoro-1H-indole-2,3-dione (443-69-6) → 3-(5-fluoro-2-oxoindolin-3-ylideneamino)-2-thioxothiazolidin-4-one (1448049-08-8)

Conditions	Yield
In ethanol for 1h; Reflux;	85%

5-(morpholin-4-ylsulfonyl)-1H-indole-2,3-dione (220510-03-2) + 3-aminorhodanine (1438-16-0) → 3-(5-(morpholinosulfonyl)-2-oxoindolin-3-ylideneamino)-2-thioxothiazolidin-4-one

Conditions	Yield
With acetic acid for 2h; Reflux;	85%

3-aminorhodanine (1438-16-0) + phosphoric acid triphenyl ester (115-86-6) + 1-phenyl-3-(4-chlorophenyl)-4-pyrazolecarboxaldehyde (36663-00-0) → C31H24ClN4O4PS2

Conditions	Yield
With lithium perchlorate In acetonitrile at 20℃; for 72h;	85%

3-aminorhodanine (1438-16-0) + 4-chlorobenzaldehyde (104-88-1) → 3-(4-chlorobenzylideneamino)-2-thioxothiazolidin-4-one (17492-66-9)

Conditions	Yield
With aluminum oxide for 0.0611111h; Microwave irradiation; Neat (no solvent);	84%
In ethanol

Indole-3-carboxaldehyde (487-89-8) + 3-aminorhodanine (1438-16-0) → (E)-3-(((1H-indol-3-yl)methylene)amino)-2-thioxothiazolidin-4-one

Conditions	Yield
In ethanol at 20℃;	84%

3-aminorhodanine (1438-16-0) + phthalic anhydride (85-44-9) → 3-(1,3-Dioxoisoindolin-2-yl)-2-thioxothiazolidin-4-on (182558-48-1)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Heating;	83%

3-aminorhodanine (1438-16-0) + N-(2,6-dimethoxy pyrimidin-4-yl)-4-isothiocyanatobenzenesulfonamide → N-(2,6-dimethoxypyrimidin-4-yl)-4-[3-(4-oxo-2-thioxothiazolidin-3-yl)thioureido]benzenesulfonamide

Conditions	Yield
With triethylamine In 1,4-dioxane for 1h; Reflux;	83%

3-aminorhodanine (1438-16-0) + 4-methyl-1,2-diaminobenzene (496-72-0) → 2-mercapto-5-methylbenzimidazole (27231-36-3)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene Heating;	83%

3-aminorhodanine (1438-16-0) + indole-2,3-dione (91-56-5) → (Z)-3-amino-5-(2-oxoindolin-3-ylidene)-2-thioxothiazolidin-4-one

Conditions	Yield
With acetic acid In ethanol at 100℃; for 0.0833333h; Temperature; Solvent; Knoevenagel Condensation; Microwave irradiation;	83%
With ammonium chloride In ethanol at 100℃; for 5.16667h; Knoevenagel Condensation;	72%
In ethanol at 100℃; Knoevenagel Condensation; Reflux;	72%

Upstream product

• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 471-32-9 dithiocarbonic acid hydrazide 
• 105-39-5 chloroacetic acid ethyl ester 
• 20469-71-0 dithiocarbonic acid hydrazide, hydrazonium salt 
• 79-11-8 chloroacetic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 7732-18-5 water 

Downstream Products

• 52514-13-3 3-{[(2E)-3-phenylprop-2-en-1-ylidene]amino}-2-thioxo-1,3-thiazolidin-4-one 
• 19745-84-7 3-amino-5-trans-cinnamylidene-2-thioxo-thiazolidin-4-one 
• 19745-90-5 5-trans-cinnamylidene-3-trans-cinnamylidenamino-2-thioxo-thiazolidin-4-one 
• 20904-81-8 N,N-Diacetylamino-rhodanin 
• 17592-96-0 3-amino-5-(4-nitro-benzylidene)-2-thioxo-thiazolidin-4-one 
• 17592-95-9 3-(4-nitro-benzylideneamino)-2-thioxo-thiazolidin-4-one 
• 4992-29-4 3-amino-5-benzylidene-2-thioxo-thiazolidin-4-one 
• 4992-28-3 3-Benzylidenamino-rhodanin 
• 4992-30-7 5-Benzyliden-3-benzylidenaminorhodanin 
• 35533-29-0 3-(2-hydroxy-benzylideneamino)-2-thioxo-thiazolidin-4-one 
• 13097-06-8 N-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzamide 
• 99985-11-2 3-amino-2-thioxo-5-vanillylidene-thiazolidin-4-one 
• 99985-12-3 (E)-4-(2-(4-hydroxy-3-methoxybenzylidene)hydrazinyl)-5-thioxodihydrothiophen-3(2H)-one 
• 82220-83-5 4-nitro-benzoic acid-(4-oxo-2-thioxo-thiazolidin-3-ylamide) 

Relevant articles and documents

Optimizing the reversibility of hydrazone formation for dynamic combinatorial chemistry

Hydrazones from hydrazines bearing electron withdrawing groups, and aromatic or aliphatic aldehydes form and hydrolyse rapidly in water at neutral pH.

Hydrazides and hydrazines of thiazoliden sequence

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