2-Amino-1-benzylbenzimidazole → HCID 66850533, compound

HRID 252201Notes

Reaction equation

HRID 252201 reaction equation
[Br:1][CH2:2][CH:3]([OH:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:13][C:14]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]=1>C1(C)C=CC=CC=1>[BrH:1].[CH2:19]([N:18]1[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH2:2][CH:3]([OH:12])[CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:14]1=[NH:13])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 1707422-Amino-1-benzylbenzimidazoleHCID 113906081-bromo-3-phenoxy-propan-2-ol

Product 1

HCID 66850533HCID 66850533, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-bromo-3-phenoxy-propan-2-ol (5) (248 mg., 1.07 mmol.) in toluene (2 mL.) was added 2-amino-1-benzylbenzimidazole (3) (200 mg., 0.90 mmol) and the mixture was heated at reflux overnight under N2 gas. The reaction mixture was cooled to room temperature and filtered. Crystallization of the collected solid from isopropanol gave 1 as white crystals (85 mg., 23%). Recrystallization of the mother liquor afforded additional 1 as white crystals (70 mg., 19%). 1H-NMR (DMSO-d6) δ 4.12 (s, 2H), 4.33 (s, 1H), 4.43 (s, 2H), 5.57 (s, 2H), 6.96 (m, 3H), 7.21-7.38 (m, 10H), 7.46 (d, J=8.0 Hz, 1H), 7.62 (d, J=7.6 Hz, 1H), 9.18 (s, 2H); 13C-NMR (DMSO-d6) δ 45.58, 46.10, 66.54, 69.43, 110.53, 111.11, 120.71, 123.39, 123.47, 127.11, 127.91, 128.72, 129.39, 129.45, 130.39, 134.56, 150.27, 157.67, 158.33.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight under N2 gas
  3. filtrationfiltered
  4. customCrystallization of the collected solid from isopropanol

Sources & evidence

ORD record
ord-edebb761a8ae4ce5915cbf3f1036394c
Source dataset
uspto-grants-2011_01
Patent number
US07868028B2

Reaction notes

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