Water → HCID 2818217, compound

HRID 1679092Notes

Reaction equation

HRID 1679092 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[SH-:6].[Na+].C([O:10][C:11](=[O:15])[CH2:12][C:13]#[N:14])C.C(N([CH2:21][CH3:22])CC)C.[OH2:23]>>[C:21]([NH:14][C:13]1[S:6][CH:2]=[C:3]([CH3:4])[C:12]=1[C:11]([OH:10])=[O:15])(=[O:23])[CH3:22]

Participants

6

Reactant 5

HCID 962WaterHCID 6571ChloroacetoneHCID 7764Ethyl cyanoacetateHCID 8471TriethylamineHCID 28015Sodium hydrosulfide

Product 1

HCID 2818217HCID 2818217, compound

Procedure

Chloracetone was reacted with sodium hydrosulphide in h aqueous medium, and the resulting solution was treated with ethylcyanoacetate in the presence of triethylamine at the boil. Addition of water precipitated 2-amino-3-ethoxycarbonyl-4-methylthiophene which was acetylated and then heated with an aqueous solution of sodium hydroxide to give 2-acetylamino-4-methylthiophene-3-carboxylic acid. This was decarboxylated by heating in N:N-diethylaniline at 220° C, the product dinitrated in sulphuric acid medium at -5° C, and then deacetylated by heating in an aqueous solution of sulphuric acid.

Workup

  1. customprecipitated 2-amino-3-ethoxycarbonyl-4-methylthiophene which
  2. temperatureheated with an aqueous solution of sodium hydroxide

Sources & evidence

ORD record
ord-ad3ae55962c44646ab73bbb6ea96a28c
Source dataset
uspto-grants-1978_03
Patent number
US04079050

Reaction notes

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