Water → 4H-1,4-Benzothiazin-3-one

HRID 1638546Notes

Reaction equation

HRID 1638546 reaction equation
Br[CH2:2][C:3](Br)=[O:4].[SH:6][C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9].O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[O:4]=[C:3]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[S:6][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 87132-AminothiophenolHCID 61147Bromoacetyl bromide

Product 1

HCID 213964H-1,4-Benzothiazin-3-one

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Procedure

A solution of bromo acetylbromide in toluene (20 ml) was added dropwise to an ice-cooled stirred solution of 0-mercaptoaniline (10 mmol, 2.5 g) in a mixture of pyridine and toluene (50 ml, 30 ml). The mixture was allowed to heat to room temperature and stirring was continued for 2 hours followed by reflux for 30 min., whereafter water (100 ml) was added. The organic phase was separated, dried (MgSO4) and evaporated to give 3,4-dihydro-3-oxo-2H-1,4-benzothiazine. M.p. 170°-171° C.

Workup

  1. temperaturecooled
  2. additionwas added
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-3b736bec486240b195e2c265fa159ea2
Source dataset
uspto-grants-1989_11
Patent number
US04880799

Reaction notes

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