Difluoroacetic acid → HCID 66698044, compound

HRID 1619772Notes

Reaction equation

HRID 1619772 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13].[F:14][CH:15]([F:19])[C:16](O)=O>O>[F:14][CH:15]([F:19])[C:16]1[NH:8][C:7]2[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]([O:12][CH3:13])[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 9788Difluoroacetic acidHCID 12194374HCID 12194374, compound

Product 1

HCID 66698044HCID 66698044, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2,3-diamino-5-nitroanisole (Horner et al., Annalen 1953, 579, 212) (1.10 g, 6 mmol) and difluoroacetic acid (2.31 g, 24 mmol) in polyphosphoric acid (PPA) (50 g) was heated at 130° C. in an oil bath for 1 hr. The hot solution was poured into water, and the pH was adjusted to neutral with cooling to give 2-(difluoromethyl)-4-methoxy-6-nitro-1H-benzimidazole (1.33 g, 91%): mp (EtOH/H2O) 192-194° C.; 1H NMR (DMSO-d6) 314.18 (br, exchangeable with D2O, 1H), 8.18 (br, 1H), 7.65 (dd, J=1.4 Hz, 1H), 7.30 (t, JHF=52.9 Hz, 1H), 4.07 (s, 3H); Anal. Calcd. for C9H7F2N3O3: C, 44.45; H, 2.9; N, 17.3. Found: C, 44.75; H, 3.0; N, 17.3%.

Workup

  1. temperaturewith cooling

Sources & evidence

ORD record
ord-bc8cfb5b3ccf48a782cb35db7ab92191
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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