Dichloroacetyl chloride → HCID 17879223, compound

HRID 1636564Notes

Reaction equation

HRID 1636564 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[Cl:17][CH:18]([Cl:22])[C:19](Cl)=[O:20]>C1C=CC=CC=1>[ClH:17].[Cl:17][CH:18]([Cl:22])[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1)=[O:20]

Participants

4

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 2344752-(4-Aminophenyl)benzothiazole

Product 1

HCID 17879223HCID 17879223, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2(4'-aminophenyl)benzothiazole (0.4 g, 1.77 mmol) in benzene (20 ml) was added dropwise dichloroacetyl chloride (0.34 ml) at 80° C. The yellow precipitate was formed and the mixture was stirred at 80° C. for 30 minutes. The precipitate was filtered off, washed with benzene and diethyl ether to give (2-(4'-dichloroacetamidophenyl) benzothiazole hydrochloride as a yellow powder (0.56 g, 84,8%). A fine powder of the above salt (0.25 g) was treated with 10% aqueous Na2CO3 (15 ml) for 50° C. for 1 hour, the product was collected by filtration, washed with water and dried to afford a white powder (0.2 g, 88.6%), m.p. 223.0-225.2° C.

Workup

  1. customThe yellow precipitate was formed
  2. filtrationThe precipitate was filtered off
  3. washwashed with benzene and diethyl ether

Sources & evidence

ORD record
ord-73e4b76a295f4c99a63808b2185ecf54
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Reaction notes

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