Ammonia → HCID 19806786, compound

HRID 1681461Notes

Reaction equation

HRID 1681461 reaction equation
[CH2:1]([O:3][C:4]1[C:8](Br)=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:6](=[O:15])[N:5]=1)[CH3:2].[NH3:16]>C(#N)C>[CH2:1]([O:3][C:4]1[C:8]([NH2:16])=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:6](=[O:15])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19806730HCID 19806730, compound

Product 1

HCID 19806786HCID 19806786, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-Ethoxy-4-bromo-5-ethoxycarbonylisothiazole-1-oxide (1.48 g, 5.0 mmol) was dissolved in fifteen ml of dry acetonitrile. The solution was cooled in ice and a solution of anhydrous ammonia in cold acetonitrile (0.105 mol in 5 ml) was added dropwise in excess. After stirring in the ice bath for 41/4 hours the reaction was complete. The title compound (1.16 g 78%, mp 153.5°-155° C.) was obtained as a yellow solid by chromatography on silica gel (chloroform).

Workup

  1. temperatureThe solution was cooled in ice

Sources & evidence

ORD record
ord-94e5a1ffcbc349dcac611188c83e3203
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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