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

HRID 1902442Notes

Reaction equation

HRID 1902442 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 hold 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 and 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 hold 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
  4. dry with materialeach time, dried over magnesium sulphate
  5. customevaporated
  6. washfor the elution

Sources & evidence

ORD record
ord-449f61b07b264062aa66db83f455f6cd
Source dataset
uspto-grants-1982_12
Patent number
US04363762

Reaction notes

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