Water → HCID 13784631, compound

HRID 235644Notes

Reaction equation

HRID 235644 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][CH2:13][CH2:14][CH:15]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16]1)=O)C.O>CCOCC>[OH:9][CH2:10][CH2:12][CH2:13][CH2:14][CH:15]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 13784630HCID 13784630, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13784631HCID 13784631, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 0.46 g of lithium aluminum hydride in 50 ml of ether was added dropwise, with ice-cooling, a solution of 1.6 g of 2-(3-ethoxycarbonylpropyl)-2H-1,4-benzothiazin-3(4H)-one in ether (30 ml). After the mixture was stirred for one hour, water was added dropwise thereto. The resultant white precipitates were filtered off, and the filtrate was dried (MgSO4). The solvent was evaporated off, and the residue was subjected to a column chromatography on silica-gel (70 g). From the eluate with hexane-ethyl acetate (1:1, v/v) was obtained 0.75 g (55.6%) of 2-(4-hydroxybutyl)-2H-1,4-benzothiazin-3(4H)-one. Recrystallization from ethyl acetate gave prisms, m.p. 101°-102° C.

Workup

  1. additionwas added dropwise, with ice-
  2. temperaturecooling
  3. customThe resultant white precipitates
  4. filtrationwere filtered off
  5. dry with materialthe filtrate was dried (MgSO4)
  6. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-64106dae4adf4cc2b2c3433398b68704
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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