Dichloromethane → 5'-Chloro-4-ethoxy-2'-hydroxy-3-thiophenecarboxanilide

HRID 614210Notes

Reaction equation

HRID 614210 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.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([OH:23])=[C:20]([CH:22]=1)[NH2:21]>C(N(CC)CC)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([OH:23])=[C:20]([CH:22]=1)[NH:21][C:9]([C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:8][S:7][CH:6]=1)=[O:10]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 72652-Amino-4-chlorophenolHCID 125737274-Ethoxy-3-thiophenecarbonyl chloride

Product 1

HCID 213159805'-Chloro-4-ethoxy-2'-hydroxy-3-thiophenecarboxanilide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

An 8.8 g. portion of 4-ethoxy-3-thiophenecarbonyl chloride is dissolved in 100 ml. of methylene chloride and added dropwise to a mixture of 6.6 g. of 5-chloro-2-hydroxyaniline in 100 ml. of methylene chloride and 6.5 ml. of triethylamine. This mixture is stirred at ambient temperature overnight, concentrated to 100 ml. and filtered. The filtrate is allowed to stand overnight and the precipitate which forms is collected, washed with water and dried in vacuo. This combined precipitate is recrystallized from 200 ml. of ethanol, treated with charcoal, filtered through diatomaceous earth and concentrated giving 5'-chloro-4-ethoxy-2'-hydroxy-3-thiophenecarboxanilide as red brown crystals.

Workup

  1. concentrationconcentrated to 100 ml
  2. filtrationand filtered
  3. waitto stand overnight
  4. customthe precipitate which forms is collected
  5. washwashed with water
  6. customdried in vacuo
  7. customThis combined precipitate is recrystallized from 200 ml
  8. additionof ethanol, treated with charcoal
  9. filtrationfiltered through diatomaceous earth
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-862aea1c7d194c82b153557f6da43e53
Source dataset
uspto-grants-1979_03
Patent number
US04144235

Reaction notes

Loading…