2-Amino-4-chlorobenzenethiol → HCID 45381536, compound

HRID 1402837Notes

Reaction equation

HRID 1402837 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][C:13](=O)[O:12][C:10](=[O:11])[CH2:9]2)=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[SH:24]>ClCCl>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]2[S:24][C:13]([CH2:14][CH:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:9][C:10]([OH:12])=[O:11])=[N:16][C:17]=2[CH:22]=1

Participants

4

Reactant 2

HCID 120002-Amino-4-chlorobenzenethiolHCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione

Product 1

HCID 45381536HCID 45381536, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-chlorophenyl)glutaric anhydride (0.5 g) and commercial 2-amino-4-chlorothiophenol (0.37 g) is dissolved in boiling dichloromethane (3 ml). The solution is stirred overnight at rt. The precipitate is isolated by suction filtration, washed with dichloromethane, and dried in vacuo. The crude product is recrystallised from acetone to give 0.3 g of 4-(5-chloro-2-benzothiazolyl)-3-(4-chlorophenyl)butanoic acid as colourless crystals.

Workup

  1. dissolutionis dissolved
  2. customThe precipitate is isolated by suction filtration
  3. washwashed with dichloromethane
  4. customdried in vacuo
  5. customThe crude product is recrystallised from acetone

Sources & evidence

ORD record
ord-08f26bda51234a58b6f552cde43f7445
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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