Water → HCID 13784627, compound

HRID 235641Notes

Reaction equation

HRID 235641 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH:10]([CH2:14][CH2:15][CH2:16][OH:17])[C:11](O)=[O:12].O>CN(C)C=O>[OH:17][CH2:16][CH2:15][CH2:14][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 20220107HCID 20220107, compound

Product 1

HCID 13784627HCID 13784627, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6.26 g of 2-aminothiophenol in 50 ml of dimethylformamide was added 9.85 g of 2-bromo 5-hydroxyvaleric acid. The mixture was stirred at room temperature for 2 hours and at 100° C. for 1 hour. The reaction solution was cooled, poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure. The concentrate was subjected to a column chromatography on silica-gel (200 g). From the eluate with hexane-acetone (2:1, v/v) was obtained 3.7 g (31.6%) of 2-(3-hydroxypropyl)-2H-1,4-benzothiazin-3(4H)-one as crystals. Recrystallization from ethyl acetate-hexane gave prisms, m.p. 59°-60° C.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a2bfec95d314090b9ab1dba7e6940ff
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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