Aniline → HCID 41532166, compound

HRID 1034278Notes

Reaction equation

HRID 1034278 reaction equation
C[Al](C)C.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N)C1C=CC=CC=1.[N:20]1([CH2:29][C:30]2[CH:40]=[CH:39][C:33]([C:34](OCC)=[O:35])=[CH:32][CH:31]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[CH:21]1>>[C:6]1([NH:5][C:34](=[O:35])[C:33]2[CH:32]=[CH:31][C:30]([CH2:29][N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[N:22]=[CH:21]3)=[CH:40][CH:39]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 7504BenzylamineHCID 16682925TrimethylaluminumHCID 57061118HCID 57061118, compound

Product 1

HCID 41532166HCID 41532166, compoundYield 13%

Procedure

Utilising a modification of the procedure described in Example 8 employing 4 equivalents of trimethylaluminium and 4 equivalents of aniline (0.67 g, 7.2 mmol) in lieu of benzylamine with respect to 1 equivalent of ethyl 4-(1H-benzimidazylmethyl)benzoate yielded a crude product was purified by column chromatography (flash silica gel, gradient elution 0-100% ethyl acetate in hexane) and recrystallised from methanol to give N-phenyl 4-(1H-benzimidazylmethyl)benzamide (75 mg, 13%) as a white crystalline solid.

Workup

  1. customyielded a crude product
  2. customwas purified by column chromatography (flash silica gel, gradient elution 0-100% ethyl acetate in hexane)
  3. customrecrystallised from methanol

Sources & evidence

ORD record
ord-b901c4af7dde48d6bd1ce4495d9035e2
Source dataset
uspto-grants-1994_05
Patent number
US05314880

Reaction notes

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