4-Hydroxybenzoic Acid → 2-(4-Hydroxyphenyl)benzothiazole

HRID 728994Notes

Reaction equation

HRID 728994 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1O.[OH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=O)=[CH:12][CH:11]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[S:34](O)(=O)=O>C(=O)(O)[O-].[Na+]>[OH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]2[S:34][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 58012-AminophenolHCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 957452-(4-Hydroxyphenyl)benzothiazoleYield 101.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3.7 g 2-aminophenol, 4.2 g 4-hydroxybenzoic acid, 4.5 g phosphorus pentoxide and 45 g methanesulfonic acid was stirred for one hour at room temperature and then heated at 90° C. for 10 hours. The reaction mixture was poured slowly into 750 ml 5% sodium bicarbonate solution. The solid which precipitated was collected and dried to give 7.0g 2-(4-hydroxyphenyl)-benzothiazole.

Workup

  1. temperatureheated at 90° C. for 10 hours
  2. customThe solid which precipitated
  3. customwas collected
  4. customdried

Sources & evidence

ORD record
ord-227d0c82f28743d0822ff40006a1d1a9
Source dataset
uspto-grants-1991_09
Patent number
US05051437

Reaction notes

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