1,1'-Carbonyldiimidazole → Ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate

HRID 1675774Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>C1COCC1>[O:21]=[C:20]1[N:8]([C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of ethyl 4-[(2-aminophenyl)amino]benzoate from Step B (442 mg, 1.72 mmol) and 1,1′-carbonyldiimidazole (652 mg, 4.02 mmol) in THF (10 mL) was heated at 75° C. for 3 h. The cooled mixture was partitioned between EtOAc (100 mL) and 10% aqueous citric acid (50 mL). The organic layer was washed with H2O (30 mL), then brine (30 mL), then dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-95:5 to 75:25, to give the title compound. MS: m/z=283 (M+1).

Workup

customThe cooled mixture was partitioned between EtOAc (100 mL) and 10% aqueous citric acid (50 mL)
washThe organic layer was washed with H2O (30 mL)
dry with materialbrine (30 mL), then dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography
washeluting with a gradient of hexane

Sources & evidence

ORD record: ord-9f7cc548c3994d988b6488f08873ad46
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003792B2

Reaction notes

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