4-Chlorobenzoyl chloride → HCID 178463788, compound

HRID 1518044Notes

Reaction equation

[NH2:1][C:2]1[C:18]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:17][C:5]2[NH:6][C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[N:8][C:4]=2[CH:3]=1.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>>[CH2:22]([N:19]([CH2:20][CH3:21])[C:18]1[C:2]([NH:1][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([Cl:24])=[CH:26][CH:27]=2)=[CH:3][C:4]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])[NH:6][C:5]=2[CH:17]=1)[CH3:23]

Participants

Reactant 2

HCID 85014-Chlorobenzoyl chloride

HCID 178463787HCID 178463787, compound

Product 1

HCID 178463788HCID 178463788, compoundYield 80.2%

Procedure

5-Amino-6-diethylamino-2-(2-methoxyphenyl)-1H-benzo[d]-imidazole (187 mg, 0.6 mmol) was reacted with 4-chlorobenzoyl chloride (105 mg, 0.6 mmol) in the same manner as that described above to give the desired product (216 mg, 80% yield) as pale yellow powder: 1H-NMR (300 MHz, CDCl3) δ 0.99 (t, 6H, J=7.2 Hz), 3.05 (q, 4H, J=7.2 Hz), 4.07 (s, 3H), 7.05 (d, 1H, J=8.4 Hz), 7.11 (t, 1H, J=7.8 Hz), 7.41 (t, 1H, J=7.8 Hz), 7.47 (d, 2H, J=8.4 Hz), 7.67 (s, 1H), 7.88 (d, 2H, J=8.4 Hz), 8.55 (d, 1H, J=6.9 Hz), 8.86 (s, 1H); 13C NMR (75 MHz, CDCl3) δ13.1, 50.6, 55.9, 111.5, 117.7, 121.7, 128.3, 129.0, 129.8, 131.1, 132.5, 133.9, 136.0, 137.7, 150.2, 156.7, 163.4; ESI MS m/z 449.2 [M+H]+.

Sources & evidence

ORD record: ord-24d4479b4c07408ea9b84968f28f3b68
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232410B2

Reaction notes

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