Benzotrichloride → 2-Phenylbenzothiazole

HRID 2419527Notes

Reaction equation

HRID 2419527 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[C:10]1([C:16](Cl)(Cl)Cl)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([C:16]2[S:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[N:2]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 7367BenzotrichlorideHCID 76794Benzenethiol, 2-amino-, hydrochloride (1:1)

Product 1

HCID 134392-PhenylbenzothiazoleYield 33.1%

Procedure

As in Example 1b, 16.2 g (0.1 mol) of 2-aminothiophenol hydrochloride is reacted at 180° C bath temperature with 19.5 g (0.1 mol) of benzotrichloride (B). By extracting the reaction products with benzene and chromatographing the benzene extract on an Al2O3 column, 7.0 grams of Compound II were obtained, M.P. 105°-110° C (33% of the theory). A small specimen was recrystallized from ethanol: M.P. 113°-114° C.

Workup

  1. extractionBy extracting the reaction products with benzene and chromatographing the benzene
  2. extractionextract on an Al2O3 column

Sources & evidence

ORD record
ord-4c46e46dfadd40b5afd93ddd6258f7b2
Source dataset
uspto-grants-1978_08
Patent number
US04107169

Reaction notes

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