Sodium borohydride → (+/-)-2,7-Dichloro-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-ol

HRID 324490Notes

Reaction equation

HRID 324490 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[S:5][C:6]2[CH:13]=[CH:12][C:11]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:10]=3[C:9](=[O:19])[C:7]=2[N:8]=1>CO.ClCCl>[Cl:3][C:4]1[S:5][C:6]2[CH:13]=[CH:12][C:11]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:10]=3[CH:9]([OH:19])[C:7]=2[N:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 220036212,7-Dichloro-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

Product 1

HCID 70113755(+/-)-2,7-Dichloro-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (0.159 g) was added to a suspension of the product from step (vi) (1.27 g) in methanol (20 ml) and dichloromethane (5 ml) at room temperature. After 3 h the mixture was partitioned between 2N NaOH and dichloromethane. The organic phase was collected, dried, (MgSO4) and solvent evaporated to leave a colourless foam. Yield: 1.27 g Used directly in the next step.

Workup

  1. customAfter 3 h the mixture was partitioned between 2N NaOH and dichloromethane
  2. customThe organic phase was collected
  3. customdried
  4. custom(MgSO4) and solvent evaporated
  5. customto leave a colourless foam

Sources & evidence

ORD record
ord-3730e788ac444b46a21c70c556d18e6f
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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