Diethyl Ether → HCID 178502033, compound

HRID 1294082Notes

Reaction equation

[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:20]=[CH:19][C:10]3[NH:11][C:12]([NH:14][C:15](=[O:18])[O:16][CH3:17])=[N:13][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[O:32])[CH:27]=[CH:28][CH:29]=1.C(OCC)C>C1COCC1>[Cl:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]([NH:1][C:2]2[CH:22]=[CH:21][C:5]([O:6][C:7]3[CH:20]=[CH:19][C:10]4[NH:11][C:12]([NH:14][C:15](=[O:18])[O:16][CH3:17])=[N:13][C:9]=4[CH:8]=3)=[CH:4][CH:3]=2)=[O:32])[CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of methyl (5-(4aminophenoxy)-1H-benzimidazol-2-yl)carbamate (Intermediate 3) (80 mg, 0.27 mmol) and 3-chlorophenylisocyanate (49 mg, 0.32 mmol) in dry THF (2 ml) was heated to 45° C. overnight. After cooling, diethyl ether was added to form a precipitate. The solid was collected by filtration to provide the title compound (83 mg, 69%): 1H NMR (DMSO-d6) δ 11.60 (brs, 2H), 9.00 (s, 1H), 8.83 (s, 1H), 7.70 (m, 1H), 7.42 (d, 2H), 7.38 (d, 1H), 7.32–7.24 (m, 2H), 7.01 (m, 2H), 6.93 (d, 2H), 6.80 (dd, 1H) 3.75 (s, 3H); MS m/e 452 (M+1).

Workup

temperatureAfter cooling
customto form a precipitate
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-a0d917b2b0614eb18ddde1bc0e0a7c8d
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238813B2

Reaction notes

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