Ammonia → HCID 14601662, compound

HRID 1638290Notes

Reaction equation

HRID 1638290 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:21]=1.[C:22](Cl)(Cl)=[O:23].[NH3:26]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:15][CH2:16][CH:17]([O:20][C:22](=[O:23])[NH2:26])[CH2:18][CH2:19]3)=[O:13])[C:6]=2[CH:21]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6371PhosgeneHCID 3082453Hpr 611

Product 1

HCID 14601662HCID 14601662, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 5-chloro-3-(4-hydroxypiperidinocarbonylmethyl)benzothiazolin-2-one (3.2 g) in dry dioxane (70 ml) was gradually dropped in a phosgene solution in dry dioxane (10 ml), under cooling. The mixture was left for two hours at room temperature. After cooling, to the mixture was gradually dropwise added 28% aqueous ammonia (5 ml) and the resultant was stirred for two hours at room temperature. Dioxane was evaporated off under vacuum from the reaction mixture. The residue was washed with water and then recrystallized from a mixture of dioxane and ethanol to yield the title compound as colorless crystals (2.8 g). m.p. 210°-212° C.

Workup

  1. temperatureunder cooling
  2. temperatureAfter cooling, to the mixture
  3. customDioxane was evaporated off under vacuum from the reaction mixture
  4. washThe residue was washed with water
  5. customrecrystallized from a mixture of dioxane and ethanol

Sources & evidence

ORD record
ord-2ca16ae4225a4719995a1777bf5e5d9b
Source dataset
uspto-grants-1989_11
Patent number
US04879301

Reaction notes

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