Acetic Acid → HCID 3300302, compound

HRID 235638Notes

Reaction equation

HRID 235638 reaction equation
C([O:3][C:4]([CH:6]1[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7]1)=O)C.[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[OH:3][CH2:4][CH:6]1[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3749252HCID 3749252, compoundHCID 4311764Sodium borohydride

Product 1

HCID 3300302HCID 3300302, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 3.0 g of 2-ethoxycarbonyl-2H-1,4-benzothiazin-3(4H)-one in ethanol (50 ml) was added portionwise 0.95 g of sodium borohydride with stirring at room temperature. After stirring for 2 hours, the mixture was diluted with water, made acidic with acetic acid, and extracted with ether. The ether layer was washed with water, dried (MgSO4), and then concentrated under reduced pressure. The residue was washed with hexane to obtain 1.25 g (50.8%) of 2-hydroxymethyl-2H-1,4-benzothiazin-3(4H)-one as crystals. Recrystallization from ethyl acetate gave prisms, m.p. 156°-157° C.

Workup

  1. stirringAfter stirring for 2 hours
  2. extractionextracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-8112d99edfa94a7a8f17782fd9133d4a
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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