Bromoacetic Acid → 5-chloro-2H-benzo[b][1,4]thiazin-3(4H)-one

HRID 1157003Notes

Reaction equation

HRID 1157003 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[SH:9].Br[CH2:11][C:12](O)=[O:13]>[OH-].[Na+].O>[Cl:8][C:7]1[C:2]2[NH:1][C:12](=[O:13])[CH2:11][S:9][C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6227Bromoacetic AcidHCID 126786672-Amino-3-chlorobenzene-1-thiol

Product 1

HCID 128992635-chloro-2H-benzo[b][1,4]thiazin-3(4H)-oneYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Amino-3-chlorothiophenol (2.5 g) was dissolved in a solution of sodium hydroxide (690 mg) in water (40 ml), and bromoacetic acid (2.4 g) was added thereto with stirring. After stirring at 70° C. for 3 hours, the precipitated crystals were filtered, washed with water and dried to obtain 2.98 g of the objective 5-chloro-2,3-dihydro-1,4-benzothiazine-3-one (m.p. 160°-161° C.).

Workup

  1. additionwas added
  2. stirringAfter stirring at 70° C. for 3 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5197b60a4bce43fea2434a7b6679992a
Source dataset
uspto-grants-1982_06
Patent number
US04337357

Reaction notes

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