Water → 3-Carbomethoxy-4-[(chloroacetyl)amino]thiophene

HRID 67580

Reaction equation

HRID 67580 reaction equation
Cl.[C:2]([C:6]1[C:10]([NH2:11])=[CH:9][S:8][CH:7]=1)([O:4][CH3:5])=[O:3].[Cl:12][CH2:13][C:14](Cl)=[O:15].C(N(CC)CC)C.O>C(Cl)Cl>[C:2]([C:6]1[C:10]([NH:11][C:14](=[O:15])[CH2:13][Cl:12])=[CH:9][S:8][CH:7]=1)([O:4][CH3:5])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2777609Methyl 4-aminothiophene-3-carboxylate Hydrochloride

Product 1

HCID 145100033-Carbomethoxy-4-[(chloroacetyl)amino]thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 12.2 g (0.063 mol) of 3-carbomethoxy-4-aminothiophene hydrochloride in 100 ml of methylene chloride is treated with 10 ml (0.126 mol) of chloroacetyl chloride and subsequently dropwise with 17.6 ml (0.126 mol) of triethylamine, the temperature being held below 25° C. The solution is poured into water and extracted twice with 50 ml of methylene chloride each time. The combined methylene chloride extracts are washed three times with 50 ml of water each time, dried over magnesium sulphate and evaporated. After chromatography on silica gel using methylene chloride for the elution, there is obtained crystalline 3-carbomethoxy-4-[(chloroacetyl)amino]thiophene of melting point 98°-100° C.

Workup

  1. custombeing held below 25° C
  2. extractionextracted twice with 50 ml of methylene chloride each time
  3. washThe combined methylene chloride extracts are washed three times with 50 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. washfor the elution

Sources & evidence

ORD record
ord-5b156a58561d446187fca9be1475557e
Source dataset
uspto-grants-1982_08
Patent number
US04346035

Linked notes

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