Triethylamine → HCID 54558090, compound

HRID 979184Notes

Reaction equation

HRID 979184 reaction equation
C(N(CC)CC)C.[NH:8]([CH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:20])(=[O:19])[NH:11]1)[NH2:9].[O:21]([C:28](Cl)=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[O:21]([C:28]([NH:9][NH:8][CH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:20])(=[O:19])[NH:11]1)=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 20201759HCID 20201759, compound

Product 1

HCID 54558090HCID 54558090, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5 g (0.05 mol) of triethylamine are added to 9.8 g (0.05 mol) of 3-hydrazino-2H,3H-1,2-benzisothiazole 1,1-dioxide in 100 ml of dioxane, and 8.6 g (0.55 mol) of phenoxycarbonyl chloride, dissolved in 25 ml of dioxane, are then added dropwise to the stirred mixture. After about 2 hours, the precipitated salt is filtered off under suction and washed with 15 ml of cold dioxane, and the combined mother liquors are evaporated down. Crystallization from ethanol gives 12.8 g (81% of theory) of 3-phenoxycarbonylhydrazino-2H,3H-1,2-benzisothiazole 1,1-dioxide of melting point 216° C.

Workup

  1. additionare then added dropwise to the stirred mixture
  2. filtrationthe precipitated salt is filtered off under suction
  3. washwashed with 15 ml of cold dioxane
  4. customthe combined mother liquors are evaporated down
  5. customCrystallization from ethanol

Sources & evidence

ORD record
ord-decbe4fe158c442c9fb0ef3709f466a1
Source dataset
uspto-grants-1987_05
Patent number
US04666930

Reaction notes

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