1,1'-Carbonyldiimidazole → 1-cyclopropyl-5,6-difluoro-1H-benzo[d]imidazol-2(3H)-one

HRID 1048963Notes

Reaction equation

HRID 1048963 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH:13]1([NH:16][C:17]2[C:18]([NH2:25])=[CH:19][C:20]([F:24])=[C:21]([F:23])[CH:22]=2)[CH2:15][CH2:14]1>C1COCC1.C(OCC)(=O)C>[CH:13]1([N:16]2[C:17]3[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=3[NH:25][C:1]2=[O:2])[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 68053726N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine

Product 1

HCID 666935521-cyclopropyl-5,6-difluoro-1H-benzo[d]imidazol-2(3H)-oneYield 68.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Carbonyldiimidazole (4.3 g) was added to the solution of N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine (3.2 g) in THF (30 ml). The mixture was stirred at rt for 20 hours, then diluted with ethyl acetate (200 ml) and washed with hydrochloric acid (1M, 200 ml). Organic layer dried over sodium sulphate, solvent removed to give expected product as a black solid (2.5 g). 1H NMR (CD3OD)δ: 7.20 (dd, 1H), 6.95 (dd, 1H), 2.86 (m, 1H), 1.11 (m, 2H), 0.94 (m, 2H).

Workup

  1. washwashed with hydrochloric acid (1M, 200 ml)
  2. dry with materialOrganic layer dried over sodium sulphate, solvent
  3. customremoved

Sources & evidence

ORD record
ord-471d23be7c0c49198a882315f7189648
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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