Acetic Acid → N-((1H-Benzo[d]imidazol-5-yl)methyl)benzenamine

HRID 45974Notes

Reaction equation

HRID 45974 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 100120381H-1,3-benzodiazole-5-carbaldehyde

Product 1

HCID 178420490N-((1H-Benzo[d]imidazol-5-yl)methyl)benzenamine

Procedure

The compound was synthesized starting from benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.), aniline (0.095 ml; 1 mmol; 1 eq.), NaBH(AcO)3 (318 mg; 1.5 mmol; 1.5 eq.) and AcOH (0.095 ml; 1.5 mmol; 1.5 eq.) as described above. Yield: 0.160 g (71%); MS m/z: 224.3 [M+H]+; 1H-NMR (400 MHz, DMSO d6): δ 4.34-4.35 (m, 2H); 6.20.6.21 (m, 1H); 6.45-6.49 (m, 1H); 6.57-6.59 (m, 1H); 6.98-7.02 (m, 1H); 7.17-7.26 (m, 2H); 7.39-7.43 (m, 1H); 7.49-7.52 (m, 2H); 12.34-12.39 (br m, 1H); HPLC (METHOD [A]): rt 8.16 min (97.3%)

Workup

  1. customThe compound was synthesized
  2. customrt 8.16 min (97.3%)

Sources & evidence

ORD record
ord-5502873ea50842278b7fe138d4c2f553
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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