4-Toluenesulfonyl chloride → HCID 12917757, compound

HRID 1156957Notes

Reaction equation

HRID 1156957 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH:14]1[C:19]2[N:20]=[CH:21][S:22][C:18]=2[CH2:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[S:7]([O:12][CH2:13][CH:14]1[C:19]2[N:20]=[CH:21][S:22][C:18]=2[CH2:17][CH2:16][CH2:15]1)([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 129177514,5,6,7-Tetrahydro-4-benzothiazolemethanol

Product 1

HCID 12917757HCID 12917757, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

9.95 g (52 mmoles) p-toluenesulfonyl chloride are added portionwise to a mixture of 8 g (47 mmoles) of the above derivative (IV) and 15 g anhydrous pyridine, while maintaining the temperature at 10° C. After stirring for 24 hrs at room temperature, the mixture is hydrolyzed and is then extracted with ethyl acetate. The combined organic phases are washed with water, dried and evaporated. The residual oil crystallizes slowly. The product is recristallyzed from boiling isopropyl oxide, on cooling. Yield: 72%. M.p.=64°-65° C.

Workup

  1. extractionis then extracted with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. customdried
  4. customevaporated
  5. customThe residual oil crystallizes slowly
  6. temperatureon cooling

Sources & evidence

ORD record
ord-6701af09dfcc4b22a3ee40cfa5444a7e
Source dataset
uspto-grants-1982_06
Patent number
US04337343

Reaction notes

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