Ammonia → HCID 178513614, compound

HRID 382352Notes

Reaction equation

HRID 382352 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[NH3:23].Cl>O1CCCC1.O.CN(C=O)C>[C:1]1([C:7]2[NH:8][C:9]3[C:15]([C:16]([NH2:23])=[O:18])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 178524243HCID 178524243, compound

Product 1

HCID 178513614HCID 178513614, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Phenylbenzimidazole-4-carboxylic acid (50 mg, 0.21 mmol) was dissolved in dry tetrahydrofuran (10 ml) and thionyl chloride (16.8 μl, 0.231 mmol) and DMF (0.05 ml) were added. The mixture was stirred at room temperature for 12 hours, when a white precipitate developed, and the suspension was added dropwise to stirred aqueous ammonia (10 ml) over 10 minutes. The mixture was stirred for a further 30 minutes, diluted with water (20 ml), and neutralised with hydrochloric acid (4M). The white solid which was precipitated upon cooling, was collected by filtration to afford 2-phenylbenzimidazole-4-carboxamide (31 mg, 62%); vmax/cm−1 3320, 3180, 1660 and 1600; δH (d6-DMSO, 200 MHz) 7.45 (1H, t, Ar-5H), 7.72 (3H, d, 3-Ph-4H), 7.87 (1H, d, Ar-4H), 7.97 (1H, br s, CONH), 7.99 (2H, d, Ar-6H), 8.38 (2H, d, Ph-2-H and Ph-2-H); 9.5 (1H, br s, CONH); m/z (EI) 237 (M+), 220, 192, 165, 77.

Workup

  1. additionthe suspension was added dropwise
  2. stirringThe mixture was stirred for a further 30 minutes
  3. customThe white solid which was precipitated
  4. temperatureupon cooling
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-84c32b03bcb440ca8ae2d88a1c345f0f
Source dataset
uspto-grants-2001_10
Patent number
US06310082B1

Reaction notes

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