Thioglycolic Acid → HCID 23372826, compound

HRID 1899072Notes

Reaction equation

HRID 1899072 reaction equation
Cl[C:2]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH:4]=O.[C:22]([OH:26])(=[O:25])[CH2:23][SH:24].C(N(CC)CC)C>N1C=CC=CC=1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:2]2[S:24][C:23]([C:22]([OH:26])=[O:25])=[CH:4][C:3]=2[C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 54157120HCID 54157120, compound

Product 1

HCID 23372826HCID 23372826, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-chloro-3-(4-fluorophenyl)-2-(4-nitrophenyl)propenal (1.5 g), thioglycolic acid (0.36 ml) and triethylamine (1.5 ml) in pyridine (7.6 ml) was stirred at 70° C. for 1 hour and refluxed for 7 hours. Pyridine was evaporated, and the residue was dissolved in ethyl acetate, washed with water and dilute hydrochloric acid, dried and concentrated. The residue (1.6 g) was washed with toluene to give pale brown crystals of 5-(4-fluorophenyl)-4-(4-nitrophenyl)thiophene-2-carboxylic acid (1.1 g).

Workup

  1. temperaturerefluxed for 7 hours
  2. customPyridine was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and dilute hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. washThe residue (1.6 g) was washed with toluene

Sources & evidence

ORD record
ord-9d836102816e49d382c09db0b95a551d
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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