3-Fluorophenyl isocyanate → HCID 22728619, compound

HRID 2084988Notes

Reaction equation

HRID 2084988 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:33]([NH:32][C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=4)=[O:34])[CH:17]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1230643-Fluorophenyl isocyanateHCID 516892Sodium BicarbonateHCID 9818480HCID 9818480, compound

Product 1

HCID 22728619HCID 22728619, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Indan-5-ylamino)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (Table A, Example A599; 0.08 g, 0.3 mmol) in dichloromethane (10 mL) was was treated with 3-fluorophenyl isocyanate (0.038mg, 0.3 mmol). The mixture was shaken on an orbital shaker for 72 hours. Saturated aqueous sodium bicarbonate (5 mL) was added, shaking continued for 5 minutes and the organic layer transferred directly onto a column of silica gel. Elution with dichloromethane gave the product as a yellow solid.

Workup

  1. stirringshaking
  2. waitcontinued for 5 minutes
  3. washElution with dichloromethane

Sources & evidence

ORD record
ord-dec0aba0e66344629e7a99b6c16458b8
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

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