Sodium borohydride → HCID 22595726, compound

HRID 1760531Notes

Reaction equation

HRID 1760531 reaction equation
[CH2:1]([N:4]1[C:9]2[CH:10]=[CH:11][C:12]([S:14][CH3:15])=[CH:13][C:8]=2[C:7](=[O:16])[C:6]([CH3:18])([CH3:17])[S:5]1(=[O:20])=[O:19])[CH:2]=[CH2:3].[BH4-].[Na+]>CO>[CH3:17][C:6]1([CH3:18])[CH:7]([OH:16])[C:8]2[CH:13]=[C:12]([S:14][CH3:15])[CH:11]=[CH:10][C:9]=2[N:4]([CH2:1][CH:2]=[CH2:3])[S:5]1(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22595757HCID 22595757, compound

Product 1

HCID 22595726HCID 22595726, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(prop-2-en-1-yl)-3,3-dimethyl-6-methylthio-1H-2,1-benzothiazine-4-(3H)-one 2,2-dioxide (2 g; 0.006 mol) was dissolved in methanol (40 mL) and sodium borohydride (0.45 g; 0.012 mol) was added in one portion. After the initial effervescence, the reaction was left stirring overnight. The solvent was removed under vaccuo, water added and the product extracted with chloroform. After washing the organic extracts with water, drying over magnesium sulphate and filtering, the product was isolated as a white solid (1.8 g; 90%) of 3,4-dihydro-3,3-dimethyl-6-methylthio-1-(prop-2-en-1-yl)-1H-2,1-benzothiazin-4-ol 2,2-dioxide, used immediately in the next step.

Workup

  1. waitAfter the initial effervescence, the reaction was left
  2. customThe solvent was removed under vaccuo, water
  3. additionadded
  4. extractionthe product extracted with chloroform
  5. washAfter washing the organic extracts with water
  6. dry with materialdrying over magnesium sulphate
  7. filtrationfiltering

Sources & evidence

ORD record
ord-8bd73d3cf1034ba79a772994f8ad6803
Source dataset
uspto-grants-2005_01
Patent number
US06844338B2

Reaction notes

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