Water → HCID 11666408, compound

HRID 1819748Notes

Reaction equation

HRID 1819748 reaction equation
[OH:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[H-].[Na+].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)=[O:16].O>CN(C=O)C>[O:16]=[C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[CH2:14][N:6]1[C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[S:3][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 692722-Bromo-4'-methylacetophenoneHCID 178517353HCID 178517353, compound

Product 1

HCID 11666408HCID 11666408, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-hydroxy-4,5,6,7-tetrahydrobenzothiazole (335 mg, 2.16 mmol) in DMF (3 mL) was added NaH (101 mg, 2.52 mmol). After stirring 10 minutes at room temperature, a solution of 2-bromo-4′-methylacetophenone (668 mg, 2.82 mmol) in DMF (5 mL) was added and the mixture was stirred overnight. Water was added and the mixture was extracted with EtOAc, dried over MgSO4 and the solvent was evaporated. The oil recovered was purified by flash chromatography on silicagel (CH2Cl2) to give 29 as a solid in 65% yield: mp 108-110° C.; 1H-NMR (DMSO-d6) 1.73 (s, 4H), 2.19 (s, 2H) 2.40 (m, 5H), 5.23 (s, 2H), 7.39 (d, 2H), 7.95 (d, 2H); Anal. (C16H17NO2S) C, H, N.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated
  5. customThe oil recovered
  6. customwas purified by flash chromatography on silicagel (CH2Cl2)

Sources & evidence

ORD record
ord-adcd201d24154adf8a9e77b7411c7470
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

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