Dichloromethane → 4-Ethoxy-2'-hydroxy-3-thiophenecarboxanilide

HRID 614209Notes

Reaction equation

HRID 614209 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([C:9](Cl)=[O:10])=[CH:6][S:7][CH:8]=1)[CH3:2].C(Cl)Cl.N[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([N:25](CC)CC)C>O>[CH2:1]([O:3][C:4]1[C:5]([C:9]([NH:25][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[OH:16])=[O:10])=[CH:6][S:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 2794249O-PhenylhydroxylamineHCID 125737274-Ethoxy-3-thiophenecarbonyl chloride

Product 1

HCID 125818594-Ethoxy-2'-hydroxy-3-thiophenecarboxanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1.31 g. portion of 4-ethoxy-3-thiophenecarbonyl chloride is dissolved in 10 ml. of dry methylene chloride and then added dropwise to a solution of 0.75 g. of O-aminophenol in 10 ml. of dry methylene chloride with stirring. A 1.0 ml. portion of triethylamine is added and the mixture is then stirred overnight. This mixture is poured into water, stirred for 30 minutes and extracted three times with methylene chloride. The extracts are filtered through diatomaceous earth and then diluted with petroleum ether giving a white solid. This solid is recrystallized from a mixture of 250 ml. of methylene chloride and 250 ml. of petroleum ether giving 4-ethoxy-2'-hydroxy-3-thiophenecarboxanilide as white crystals.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted three times with methylene chloride
  3. filtrationThe extracts are filtered through diatomaceous earth
  4. additiondiluted with petroleum ether giving a white solid
  5. customThis solid is recrystallized from a mixture of 250 ml

Sources & evidence

ORD record
ord-6419ec8b28eb4e0b984dc94d59da4aea
Source dataset
uspto-grants-1979_03
Patent number
US04144235

Reaction notes

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