Potassium Iodide → 5-Cyano-7-iodo-1-phenylbenzimidazole

HRID 644558Notes

Reaction equation

N[C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=1.N([O-])=O.[Na+].[I-:23].[K+].S([O-])([O-])=O.[Na+].[Na+]>Cl.O>[C:17]([C:4]1[CH:3]=[C:2]([I:23])[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1)#[N:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 7-Amino-5-cyano-1-phenylbenzimidazole (12.5 g, 53.4 mmol) in hydrochloric acid (90 ml, 25% w/v) was diazotised with a solution of sodium nitrite (3.7 g, 53.4 mmol) in water (20 ml). The resultant mixture was stirred for 30 min at 0° C. whereafter a solution of potassium iodide (14.2 g, 85.5 mmol) in water (40 ml) was added dropwise. Stirring was continued for 10 min at 0° C., and then the temperature was raised to 80° C. for 30 min. After cooling, aqueous sodium sulphite (1M) was added and the resultant mixture was extracted with dichloromethane. Column chromatographic work-up of the dried and concentrated organic extract afforded the title product (6.5 g, 35%)

Workup

additionwas added dropwise
temperatureAfter cooling
extractionthe resultant mixture was extracted with dichloromethane
customColumn chromatographic work-up of the dried
extractionconcentrated organic extract

Sources & evidence

ORD record: ord-048ced8720f441d39e3584663d659881
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700638B2

Reaction notes

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