Phosphorus oxychloride → 2-chloro-4-nitro-6-(trifluoromethyl)-1H-benzoimidazole

HRID 730767Notes

Reaction equation

[N+:1]([C:4]1[C:12]2[NH:11][C:10](=O)[NH:9][C:8]=2[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)([O-:3])=[O:2].O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:10]1[NH:9][C:8]2[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=2[N:11]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 116301554-Nitro-6-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 116375342-chloro-4-nitro-6-(trifluoromethyl)-1H-benzoimidazole

Procedure

The benzoimidazol-2-one from step (b) above (1.8 g, 7.3 mmol) reacted with POCl3 under the conditions of Example 1c to give the title compound as a yellow solid. MS (ESI, pos. ion) m/z: 266 (M+1).

Sources & evidence

ORD record: ord-88985aa2ac8e4a429fb93afd0ea8f372
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582761B2

Reaction notes

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