Chloroacetyl chloride → 2-(4'-Chloroacetamido-3-iodophenyl) benzothiazole

HRID 1636563

Reaction equation

HRID 1636563 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][C:3]=1[I:17].[Cl:18][CH2:19][C:20](Cl)=[O:21]>C1C=CC=CC=1>[Cl:18][CH2:19][C:20]([NH: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][C:3]=1[I:17])=[O:21]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 384526Benzenamine, 4-(2-benzothiazolyl)-2-iodo-

Product 1

HCID 105026782-(4'-Chloroacetamido-3-iodophenyl) benzothiazoleYield 71.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(4'-amino-3'-iodophenyl) benzothiazole (DF129) (0.15 g, 0.426 mmol) in benzene (15 ml) was added dropwise chloroacetyl chloride (0.18 g) at room temperature. A yellow precipitate was formed and the resulting mixture was stirred at 50° C. for 30 minutes, and then cooled in an ice-bath. The solid was filtered off, washed with cold benzene and petroleum ether, and dried to give a yellow powder (0.13 g, 71.2%), m.p. 192.1-193.8° C.

Workup

  1. customA yellow precipitate was formed
  2. temperaturecooled in an ice-bath
  3. filtrationThe solid was filtered off
  4. washwashed with cold benzene and petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-4e82fcd6e88542cf85eaa0570c499bcf
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Linked notes

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