Triethylamine → HCID 12106078, compound

HRID 432037Notes

Reaction equation

HRID 432037 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH2:15])[CH3:3].C(N(CC)CC)C.[CH3:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(Cl)Cl>[CH3:3][N:2]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([CH3:23])=[CH:25][CH:26]=1)[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 745066HCID 745066, compound

Product 1

HCID 12106078HCID 12106078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(N,N-Dimethylaminoethyl)-2-aminobenzimidazole (0.40 g, 1.96 mmol) was dissolved in CH2Cl2 (50 mL) and cooled to 0° C., triethylamine (2 mL) was added followed by 4-methybenzoyl chloride (0.26 g, 1.96 mmol). The reaction mixture was stirred at 0° C. for 1 h and at room temperature for an additional 1 h. The volatiles were evaporated and then the residue was purified by column chromatography using CH2Cl2-MeOH (9.8-0.2). The oily material collected (0.2 g) was dissolved in anhydrous ethyl ether and transformed to the hydrochloride salt. MS 322 (M+1). 1H NMR (DMSO): δ 2.48 (s, 3H), 2.81 and 2.86 (2s, 6H), 3.54 (m, 2H), 4.73 (m, 2H), 35 7.34 (m, 4H), 7.52 (2m, 2H), 8.14 (d, 2H), 10.79 (broad s, NH).

Workup

  1. customThe volatiles were evaporated
  2. customthe residue was purified by column chromatography
  3. customThe oily material collected (0.2 g)
  4. dissolutionwas dissolved in anhydrous ethyl ether

Sources & evidence

ORD record
ord-6efd5af1cce84fa69977b474b0c55f71
Source dataset
uspto-grants-2003_12
Patent number
US06660870B1

Reaction notes

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