2-Fluorophenyl isocyanate → HCID 22003781, compound

HRID 324271Notes

Reaction equation

HRID 324271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[CH3:11][CH:12]1[C:18]2=[N:19][C:20]3[C:25](=[O:26])[CH2:24][CH2:23][CH2:22][C:21]=3[N:17]2[CH:16]=[CH:15][CH:14]=[CH:13]1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([N:19]1[C:20]2[C:25](=[O:26])[CH2:24][CH2:23][CH2:22][C:21]=2[N:17]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]([CH3:11])[CH:18]12)=[O:10]

Participants

4

Reactant 2

HCID 855882-Fluorophenyl isocyanateHCID 22003830HCID 22003830, compound

Product 1

HCID 22003781HCID 22003781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluorophenylisocyanate (0.28 g, 2.06 mmol) was added to a solution of 6-methyl-1,2,3,4-tetrahydro-4-oxo-6H-azepino(1,2-a)benzimidazole (0.4 g, 1.87 mmol; Ohta, S. et al. Chem. Pharm. Bull. 1990, 38(2), 301) in methylene chloride (5 mL) and the reaction mixture was stirred at room temperature for 16 h. The reaction was concentrated in vacuo and purified by medium pressure chromatography, using EtOAc/MeOH as an eluent and recrystallization from EtOAc/methylene chloride to give the title compound as a solid: mp 139-141° C.; MS: 352 (MH+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by medium pressure chromatography
  3. customrecrystallization from EtOAc/methylene chloride

Sources & evidence

ORD record
ord-5741df1d9f5c475095fe2c42e5621150
Source dataset
uspto-grants-2001_04
Patent number
US06218384B1

Reaction notes

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