1-Fluoro-4-(isocyanatomethyl)benzene → HCID 68826592, compound

HRID 1723922Notes

Reaction equation

HRID 1723922 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]=[C:8]=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[C:14]2[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][C:15]=2[N:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([NH:12][C:13]2[C:14]3[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][C:15]=3[N:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[O:9])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 27333761-Fluoro-4-(isocyanatomethyl)benzeneHCID 68826227HCID 68826227, compound

Product 1

HCID 68826592HCID 68826592, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzylisocyanate (0.130 ml, 1.02 mmol) was added to a solution of 1-ethyl 5-methyl 3-amino-1H-thieno[3,2-c]pyrazole-1,5-dicarboxylate (85 mg, 0.32 mmol) in anhydrous dichloromethane (5 ml). After stirring for 96 h at room temperature, the solvent was removed under reduced pressure, and the residue purified by chromatography over silica gel (eluent dichloromethane 50; methyl alcohol 0.5; 6% aqueous ammonia 0.1) to yield 80 mg of the title compound as a white solid. Chromatographic method A, Rt 6.11, [M+H]+ 621.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue purified by chromatography over silica gel (eluent dichloromethane 50; methyl alcohol 0.5; 6% aqueous ammonia 0.1)

Sources & evidence

ORD record
ord-dcba06b3da1f4ffb9bcc9fe8c1e854b1
Source dataset
uspto-grants-2009_02
Patent number
US07485661B2

Reaction notes

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