Water → 2-(2-bromoethyl)-3,4-dihydro-2H-1,4-benzothiazin-3-one

HRID 235636

Reaction equation

HRID 235636 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH:10]([CH2:15][CH2:16][Br:17])[C:11](OC)=[O:12].O>CN(C)C=O>[Br:17][CH2:16][CH2:15][CH:10]1[C:11](=[O:12])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 87132-AminothiophenolHCID 296716Methyl 2,4-dibromobutanoate

Product 1

HCID 137846232-(2-bromoethyl)-3,4-dihydro-2H-1,4-benzothiazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.6 g of 2-aminothiophenol in 50 ml of dimethylformamide was added dropwise 9.55 g of methyl 2,4-dibromobutyrate with stirring at room temperature. After stirring one hour, the reaction mixture was poured into water to give crystals of 2-(2-bromoethyl)-2H-1,4-benzothiazin-3(4H)-one. The crystals were collected by filtration and washed with water, n-hexane and cold methanol. The yield was 6.32 g (63.3%). Recrystallization from ethyl acetate gave prisms, m.p. 151°-152° C.

Workup

  1. stirringAfter stirring one hour

Sources & evidence

ORD record
ord-66c4d911e5e844a9821e0bb40e9b853d
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Linked notes

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