Water → 2-(3-bromopropyl)-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one

HRID 235635Notes

Reaction equation

HRID 235635 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[SH:10].Br[CH:12]([CH2:17][CH2:18][CH2:19][Br:20])[C:13](OC)=[O:14].O>CN(C)C=O>[Br:20][CH2:19][CH2:18][CH2:17][CH:12]1[C:13](=[O:14])[NH:1][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=2[S:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 3006462-Amino-4,5-dimethylbenzenethiolHCID 10912698Methyl 2,5-dibromopentanoate

Product 1

HCID 137846132-(3-bromopropyl)-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-oneYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.06 g of 2-amino-4,5-dimethylthiophenol in 50 ml of dimethylformamide was added 5.48 g of methyl 2,5-dibromovalerate at room temperature with stirring. The mixture was stirred for 14 hours, poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was washed with a mixture of ether and hexane to obtain 4.35 g (69.3%) of 2-(3-bromopropyl)-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one as crystals. Recrystallization from methanol gave prisms, m.p. 151°-153° C.

Workup

  1. stirringThe mixture was stirred for 14 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washThe residue was washed with a mixture of ether and hexane

Sources & evidence

ORD record
ord-7b6ac7bd60424125b3075712dcc04934
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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