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

HRID 2286812Notes

Reaction equation

HRID 2286812 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]>O.[Zn]>[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)-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The zinc salt (2.0 g) of 2-amino-3-chlorothiophenol was suspended in water (30 ml), and bromoacetic acid (1.6 g) was added thereto, followed by stirring at 70° C. for 3 hours. The precipitated crystals were filtered, washed with water and dried to obtain 1.8 g of the objective 5-chloro-2,3-dihydro-1,4-benzothiazine-3-one (m.p. 160°-161° C.).

Workup

  1. filtrationThe precipitated crystals were filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-f9680a43eefe4c629771072ec4eece08
Source dataset
uspto-grants-1981_05
Patent number
US04268301

Reaction notes

Loading…