2,4-Dimethoxybenzylamine → HCID 178491086, compound

HRID 1765968Notes

Reaction equation

HRID 1765968 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]=2[N:4]=[C:3]1[CH:23]=O.[CH3:25][O:26][C:27]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>C(O)(=O)C.CO>[CH3:25][O:26][C:27]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:28]=1[CH2:29]/[N:30]=[CH:23]/[C:3]1[N:2]([CH3:1])[C:6]2[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]=2[N:4]=1

Participants

5

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 21107908HCID 21107908, compound

Product 1

HCID 178491086HCID 178491086, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.1 g (0.32 mmol) 1-methyl-4,7-diphenyl-1H-benzimidazole-2-carbaldehyde, 55 mg (0.32 mmol) 2,4-dimethoxybenzylamine and 1 drop glacial acetic acid in 8 ml methanol were stirred for 12 hour at room temperature. The reaction mixture was cooled to −20° C. and filtered while cold. The solid was washed with cold (−20° C.) methanol (2×1 ml) and dried at reduced pressure. Yield—0.12g (81.1%). %). 1H NMR (250 MHz, CDCl3), δ, ppm: 3.76 (s, 3H), 3.80 (s, 6H), 4.81 (s, 2H), 6.46 (m, 2H), 7.14 (d, JHH=8.8 Hz, 1H), 7.25 (d, JHH=7.6 Hz, 1H), 7.46 (m, 9H), 8.02 (d, JHH=7.0 Hz, 2H), 8.61 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to −20° C.
  2. filtrationfiltered while cold
  3. washThe solid was washed with cold (−20° C.) methanol (2×1 ml)
  4. customdried at reduced pressure
  5. customYield—0.12g (81.1%)

Sources & evidence

ORD record
ord-6be2492237dc433cb629d00e2a188b1d
Source dataset
uspto-grants-2007_06
Patent number
US07229943B2

Reaction notes

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