Pyridine → 3-Chloro-2-chloroacetylaminothiophenol

HRID 2286813Notes

Reaction equation

HRID 2286813 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[SH:9].N1C=CC=CC=1.[Cl:16][CH2:17][C:18](Cl)=[O:19]>C1C=CC=CC=1>[Cl:8][C:7]1[C:2]([NH:1][C:18](=[O:19])[CH2:17][Cl:16])=[C:3]([SH:9])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 126786672-Amino-3-chlorobenzene-1-thiol

Product 1

HCID 128992643-Chloro-2-chloroacetylaminothiophenolYield 84.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

2-Amino-3-chlorothiophenol (1.6 g) and pyridine (0.8 g) were dissolved in benzene (20 ml), and chloroacetyl chloride (1.2 g) was gradually added dropwise thereto at room temperature (25° C.) with stirring. After the addition was finished, the reaction mixture was stirred at room temperature for 30 minutes, and the solvent was removed under reduced pressure. The residue obtained was washed with water, dried and recrystallized from chloroform to obtain 2.0 g of 3-chloro-2-chloroacetylaminothiophenol (m.p. 186°-187° C.).

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. customthe solvent was removed under reduced pressure
  4. customThe residue obtained
  5. washwas washed with water
  6. customdried
  7. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-61f5a671c7424d6cad1ff35b80e85e91
Source dataset
uspto-grants-1981_05
Patent number
US04268301

Reaction notes

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