Nitric Acid → 583057-49-2

HRID 2252519Notes

Reaction equation

HRID 2252519 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][CH:9]=[C:10]([CH2:11][O:12][C@H:13]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.O.[N+:29]([O-:32])([OH:31])=[O:30]>C(O)C>[N+:29]([O-:32])([OH:31])=[O:30].[Cl:1][C:2]1[C:7]2[S:8][CH:9]=[C:10]([CH2:11][O:12][C@H:13]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962Water2×HCID 6604451Arasertaconazole

Product 1

HCID 9806019583057-49-2Yield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

880 mg (2.01 mmol) of (R)-(−)-1-[2-(7-chlorobenzo[b]thiophen-3-yl-methoxy)-2-(2,4-dichlorophenyl)-ethyl]-1H-imidazole are dissolved in 5 ml of 96% ethanol. 1 ml of water is added and heated at a temperature between 35 and 37° C. To the obtained solution, 0.23 ml of 60% nitric acid (3 mmol, 1.5 eq.) are added. Then 3 ml of water are added and cooled first at room temperature and thereafter at 10° C. for 1 hour. The formed solid is filtered, washed twice with 4 ml of water and dried at vacuum for 24 hours to give 0.9 g (R=89%) of (R)-(−)-1-[2-(7-chlorobenzo[b]thiophen-3-yl-methoxy)-2-(2,4-dichlorophenyl)-ethyl]-1H-imidazole mononitrate.

Workup

  1. temperatureheated at a temperature between 35 and 37° C
  2. filtrationThe formed solid is filtered
  3. washwashed twice with 4 ml of water
  4. customdried at vacuum for 24 hours

Sources & evidence

ORD record
ord-d04779c836fd47dba3725897b939ea03
Source dataset
uspto-grants-2008_01
Patent number
US07323433B2

Reaction notes

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