Water → HCID 13686312, compound

HRID 279763Notes

Reaction equation

HRID 279763 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 mixture was 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 filtrate were washed with water and brine, dried over MgSO4 and concentrated to a solid which was slurried in ether and filtered to give an additional 7.6 g of product, m.p. 121°-124° C. Total yield was 13.5 g.

Workup

  1. customto 0° C.
  2. customto give a gummy solid
  3. customThe water was decanted
  4. extractionextracted with ethyl acetate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0f02f0901512415ba3a61d22592afccb
Source dataset
uspto-grants-1986_05
Patent number
US04586950

Reaction notes

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