Ammonia → HCID 68153444, compound

HRID 1946936Notes

Reaction equation

HRID 1946936 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([C:15]4([CH3:22])[NH:20][C:19](=S)[CH2:18][O:17][CH2:16]4)[CH:12]=[CH:13][CH:14]=3)[O:8][C:4]=2[CH:3]=1.[NH3:25]>CO>[ClH:1].[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([C:15]4([CH3:22])[CH2:16][O:17][CH2:18][C:19]([NH2:25])=[N:20]4)[CH:12]=[CH:13][CH:14]=3)[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86668502HCID 86668502, compound

Product 1

HCID 68153444HCID 68153444, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

In a tube the (RS)-5-[3-(6-chloro-benzooxazol-2-yl)-phenyl]-5-methyl-morpholin-3-thione (260 mg, 0.7 mmol) was treated with a solution of ammonia in methanol (7M). The sealed tube was heated at 100° C. for 3 hours. For the workup, the reaction mixture was cooled to room temperature and evaporated. For purification the crude product was passed on a SCX column, and then further purified by preparative HPLC. Finally, the treatment with hydrochloric acid followed by evaporation yielded the title compound (23 mg, 9% of theory) MS (ISP): m/z=342 [M+H]+.

Workup

  1. temperatureFor the workup, the reaction mixture was cooled to room temperature
  2. customevaporated
  3. customFor purification the crude product
  4. customfurther purified by preparative HPLC
  5. customFinally, the treatment with hydrochloric acid followed by evaporation

Sources & evidence

ORD record
ord-ba8e4e6b00a349d0acb36debd2b4e291
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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