Water → HCID 13686312, compound

HRID 1607787Notes

Reaction equation

HRID 1607787 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][N:16]1[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24](Cl)[C:18]=2[S:17]1(=[O:27])=[O:26].O>CN(C)C=O>[CH3:15][N:16]1[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24]([S:14][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:18]=2[S:17]1(=[O:26])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 13686311HCID 13686311, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13686312HCID 13686312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 12 g of potassium-t-butoxide in 100 ml of dry dimethylformamide was added 12.9 mls of benzyl mercaptan at -5° to 0° C. under an inert atmosphere followed by 12.2 g of 2-methyl-7-chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide. The mixturewas stirred at room temperature for 16 hours and poured into water to give a gummy solid. The water was decanted and extracted with ethyl acetate. The gummy solid was slurried in ethyl acetate and filtered to give 5.9 g of the title compound as a light orange solid, m.p. 119°-122° C. The combined ethyl acetate extract and filtratewere washed with water and brine, dried over MgSO4 and concentrated toa solid which was slurried in either and filtered to give an additional 7.6g of product, m.p. 121°-124° C. Total yield was 13.5 g.

Workup

  1. customto give a gummy solid
  2. customThe water was decanted
  3. extractionextracted with ethyl acetate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f6a5b985c38b408ea54bafb398ceb30c
Source dataset
uspto-grants-1989_09
Patent number
US04867781

Reaction notes

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