122-07-6 Usage
Description
Methylaminoacetaldehyde dimethyl acetal is a clear colorless to light yellowish liquid that serves as a pharmaceutical synthesis intermediate. It is primarily used in the preparation of methimazole, an antithyroid drug that inhibits thyroid endoperoxide enzymes, thus hindering the synthesis of thyroxine (T4) and triiodothyronine (T3). Methylaminoacetaldehyde dimethyl acetal also plays a role in reducing the level of thyroid-stimulating antibodies in the blood circulation and restoring the function of suppressor T cells.
Uses
Used in Pharmaceutical Industry:
Methylaminoacetaldehyde dimethyl acetal is used as a pharmaceutical synthesis intermediate for the preparation of methimazole (1-methylimidazole-2-thiol), an antithyroid drug. It is utilized in this application due to its ability to inhibit thyroid endoperoxide enzymes, which in turn hinders the oxidation of iodide and the coupling of tyrosine, essential steps in the synthesis of thyroid hormones.
Used in Organic Synthesis:
Methylaminoacetaldehyde dimethyl acetal is used as a reactant in the synthesis of various organic compounds, such as Aza[3.3.2] cyclazines, N-(2,2-Dimethoxyethyl)-N-methyl-3,4-dimethoxyphenylglycine, and substituted imidazoles. It is employed in these applications due to its reactivity and ability to form functionalized intermediates, which are crucial in the synthesis of these complex molecules.
In the synthesis of Aza[3.3.2] cyclazines, it reacts with 5-methyloxazolo[3,2-a]pyridinium salts to form functionalized 5-aminoindolizines intermediates. In the preparation of N-(2,2-Dimethoxyethyl)-N-methyl-3,4-dimethoxyphenylglycine, it undergoes Petasis reaction with glyoxylic acid and 3,4-dimethoxyphenylboronic acid. Additionally, it is used in a copper-catalyzed reaction with various nitriles to produce substituted imidazoles.
Furthermore, 2,2-Dimethoxy-N-methylethanamine, an impurity formed in the synthetic process of Methimazole, highlights the importance of Methylaminoacetaldehyde dimethyl acetal in the production of this antithyroid agent.
Synthesis
In the autoclave, add 3.00 kg of chloroacetaldehyde dimethyl acetal, 30 kg of 33% methylamine methanol solution, close the autoclave valve, heat up to 130-135 ° C, and the pressure is up to 1.2 MPa, then continue to decrease, and the reaction is incubated for 6 hours. Cool down to 25°C and press into a neutralizer. The temperature was lowered to below 10°C under stirring, 3.26 kg of 40% sodium methoxide methanol solution was added dropwise, and the temperature was kept at 0-5°C for 2-3 hours. After filtration, the filter cake was washed with methanol, and the filtrate was transferred to a distillation pot. Distill methanol at atmospheric pressure until it no longer evaporates, change it to vacuum distillation, turn on brine to condense and collect the intermediate, collect 52-60°C/24mmHg fraction, obtain 2.51kg of methylaminoacetaldehyde dimethyl acetal, GC purity 94.6 %,? yield 83.1%.
Check Digit Verification of cas no
The CAS Registry Mumber 122-07-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 122-07:
(5*1)+(4*2)+(3*2)+(2*0)+(1*7)=26
26 % 10 = 6
So 122-07-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H13NO2/c1-6-4-5(7-2)8-3/h5-6H,4H2,1-3H3/p+1
122-07-6Relevant articles and documents
Preparation method of 2 -mercapto -1 - methylimidazole
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Paragraph 0020; 0030-0031; 0034-0035; 0038-0039, (2020/07/13)
The invention discloses a preparation method of electronic grade 2-sulfydryl-1-methylimidazole. The method comprises the following steps: (1) a water solution of chloroacetaldehyde dimethyl acetal andmethylamine performs tank closing reaction for 16h at 80 to 85 DEG C; cooling and pressure release are performed; a solvent is used for extraction; the solvent is concentrated; rectification under vacuum is performed to obtain an intermediate of methylaminoacetaldehyde dimethyl acetal; (2) the methylaminoacetaldehyde dimethyl acetal and t-butyl thionitrile react under the boron trifluoride catalysis; condensation reaction is performed at 50 to 70 DEG C to obtain 2-tert-butyl sulfenyl-1-methylimidazole; (3) a solvent is added into the 2-tert-butyl sulfenyl-1-methylimidazole; a catalyst and anorganic solvent are added; reaction is performed at constant temperature; after filtering, filter liquid is concentrated; then, electronic grade water crystallization is performed to obtain the product of 2-sulfydryl-1-methylimidazole. The preparation method has the advantages that the raw material price is low; the environment-friendly effect is achieved; the operation of the synthesis method issimple and convenient; the product quality conforms to application standards of electronic chemicals.
Amidation of unactivated ester derivatives mediated by trifluoroethanol
McPherson, Christopher G.,Caldwell, Nicola,Jamieson, Craig,Simpson, Iain,Watson, Allan J. B.
supporting information, p. 3507 - 3518 (2017/04/26)
A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.