Ammonia → HCID 69933965, compound

HRID 432854Notes

Reaction equation

HRID 432854 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH3:10][N:11]([C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@@H:27]1[CH3:32])[C:12]([C:14]1[S:25][C:17]2=[N:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:16]2[CH:15]=1)=[O:13].N>>[CH3:10][N:11]([C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@@H:27]1[CH3:32])[C:12]([C:14]1[S:25][C:17]2=[N:18][C:19]3[CH:24]=[CH:23][C:22]([N+:1]([O-:4])=[O:2])=[CH:21][C:20]=3[N:16]2[CH:15]=1)=[O:13]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 69932347HCID 69932347, compound

Product 1

HCID 69933965HCID 69933965, compound

Procedure

Under ice-cooling, fuming nitric acid (0.28 ml) was added to concentrated sulfuric acid (22 ml) solution of (+)-(1R,2S)-N-methyl-N-(2-methylcyclohexyl)thiazolo [3,2-a]benzoimidazole-2-carboxamide (2.2 g) and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was poured into ice water and neutralized with a 28% aqueous ammonia solution and then the resulting precipitate was collected by filtration to obtain (1R,2S)-N-methyl-N-(2-methylcyclohexyl)-6-nitrothiazolo [3,2-a]benzoimidazole-2-carboxamide. This was treated in the same manner as in Production Example 1 to obtain the title compound (242 mg).

Workup

  1. temperatureUnder ice-cooling
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-a01857ad91a44c829aaba1d4367e2d42
Source dataset
uspto-grants-2003_12
Patent number
US06664283B1

Reaction notes

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