Methanol → Phenyl isocyanate

HRID 1294057Notes

Reaction equation

HRID 1294057 reaction equation
NC1C=CC(O[C:7]2[CH:20]=[CH:19][C:10]3N[C:12](NC(=O)OC)=[N:13][C:9]=3[CH:8]=2)=CC=1.C[OH:24]>[Pd]>[C:9]1([N:13]=[C:12]=[O:24])[CH:10]=[CH:19][CH:20]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 178502032HCID 178502032, compound2×

Product 1

HCID 7672Phenyl isocyanateYield 17%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N-(5-(2-Nitro-5-pyridyloxy)-1H-benzimidazol-2-yl)acetamide (Intermediate 7) was hydrogenated under an H2 atmosphere with Pd—C (10%) in MeOH. After the reaction was complete, the solid was filtered off, and the filtrate was evaporated to give intermediate 8 (47 mg, 17%): 1H NMR (DMSO-d6) δ 11.56 (brs, 1H) 7.51 (d, 1H), 7.32 (d, 1H), 7.05 (dd, 1H), 6.97 (d, 1H), 6.74 (dd, 1H), 6.70 (d, 1H), 5.02 (br s, 2H), 3.74 (s, 3H), 7.08 (d, 2H), 6.84 (d, 1H), 6.61 (d, 1H), 3.75 (s, 3H); MS m/e 284 (M+1).

Workup

  1. filtrationthe solid was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a9ade2e284eb4555b2b36827b331abd9
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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