Hydrochloric Acid → 3-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester

HRID 2163456Notes

Reaction equation

HRID 2163456 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](Cl)(=[O:12])=[O:11])=[O:4].[CH2:14]([O:16][C:17](=[O:21])[CH2:18][NH:19][CH3:20])[CH3:15].O.Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:12])(=[O:11])[N:19]([CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:21])[CH3:20])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 95849Glycine, N-methyl-, ethyl esterHCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

Product 1

HCID 28087943-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20 G. of 3-chlorosulfonylthiophene-2-carboxylic acid methyl ester are dissolved in absolute chloroform, whereupon 21 g. of sarcosine ethyl ester are added dropwise during 10 minutes. In so doing, the mixture warms up to 50° C. After 20 minutes, the mixture is cooled, shaken once each time with water, 0.5-N hydrochloric acid and a sodium bicarbonate solution, dried and evaporated. The remaining oil is brought to crystallization with ethanol. There is obtained 3-(N-carbethoxymethyl-N-methyl-sulfamoyl)-thiophene-2-carboxylic acid methyl ester of melting point 84°-85° C.

Workup

  1. customwarms up to 50° C
  2. temperaturethe mixture is cooled
  3. dry with materiala sodium bicarbonate solution, dried
  4. customevaporated
  5. customThe remaining oil is brought to crystallization with ethanol

Sources & evidence

ORD record
ord-fbbc203ec61c493c944e867351d9aa8e
Source dataset
uspto-grants-1979_01
Patent number
US04134898

Reaction notes

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