Sodium sulfate decahydrate → 2-[(3-Phenoxybenzyl)thio]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol

HRID 1163310Notes

Reaction equation

HRID 1163310 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][S:12][C:13]1[S:14][C:15]2[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][S:12][C:13]1[S:14][C:15]2[CH:21]([OH:22])[CH2:20][CH2:19][CH2:18][C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 231118532-[(3-phenoxybenzyl)thio]-5,6-dihydro-1,3-benzothiazol-7(4H)-one

Product 1

HCID 587552452-[(3-Phenoxybenzyl)thio]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-olYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(3-phenoxybenzyl)thio]-5,6-dihydro-1,3-benzothiazol-7(4H)-one (2.50 g, 6.80 mmol) in tetrahydrofuran (50 mL) was added by portions lithium aluminum hydride (280 mg) under ice-cooling, and the mixture was stirred at the same temperature for 1 hr. Sodium sulfate decahydrate (1.5 g) was added to reaction mixture, and the mixture was stirred at room temperature for 1 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (2.20 g, yield 87%) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7160e33fca284c62ba3a2eafddae16ce
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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