Nitric Acid → 1-[2-Cyano-2-(4-phenylsulfinylphenyl)hexyl] imidazole

HRID 1863001Notes

Reaction equation

HRID 1863001 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([S:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)#[N:2].ClC1C=C(C=CC=1)C(OO)=[O:32].[N+]([O-])(O)=O.CCOCC>C(Cl)Cl>[C:1]([C:3]([C:14]1[CH:15]=[CH:16][C:17]([S:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:32])=[CH:18][CH:19]=1)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)#[N:2]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 540197231-[2-Cyano-2-(4-phenylthiophenyl)hexyl]imidazole

Product 1

HCID 234689461-[2-Cyano-2-(4-phenylsulfinylphenyl)hexyl] imidazoleYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4 g (0.01 mole) of 1-[2-cyano-2-(4-phenylthiophenyl) hexyl]imidazole in 25 ml of methylene chloride is added 2.5 g (0.012 mole) of 85% m-chloroperoxybenzoic acid in small portions at 0°. The mixture is stirred at room temperature overnight. To the reaction mixture is added conc. nitric acid until it is strongly acidic. To this solution is added 150 ml of anhydrous ether. The gummy solid precipitates are washed with ether and back neutralized with dilute NH4OH solution. The free base (3.5 g) thus obtained is a yellow solid, mp 55°-61°.

Workup

  1. customThe gummy solid precipitates
  2. washare washed with ether

Sources & evidence

ORD record
ord-cfe72728da5b48dd920b2e0fe9acf826
Source dataset
uspto-grants-1979_09
Patent number
US04167576

Reaction notes

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