Phenyl isocyanate → HCID 59300954, compound

HRID 2235447Notes

Reaction equation

HRID 2235447 reaction equation
[CH3:1][C:2]1([CH3:26])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-])=O)=[C:8]([NH:11][C:12](=O)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[NH:4][C:3]1=[O:25].[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[C:27]1([NH:33][C:34]([N:4]2[C:5]3[CH:6]=[C:7]4[N:22]=[C:12]([C:13]5[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=5)[NH:11][C:8]4=[CH:9][C:10]=3[C:2]([CH3:26])([CH3:1])[C:3]2=[O:25])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 23092680HCID 23092680, compound

Product 1

HCID 59300954HCID 59300954, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-4-methoxy-benzamide (100 mg) and phenyl isocyanate (35 mg; 0.3 mmol) in dry toluene (2 ml) is stirred in a microwave apparatus at 150° C. for 900 s. The mixture is filtered and concentrated in vacuo. The residue is dissolved in acetic acid (2 ml), iron (115 mg; powder) is added and the mixture is again stirred in a microwave apparatus at 150° C. for 900 s to achieve reduction of the nitro function and ring closure. The mixture is filtered and concentrated in vacuo. The desired compound (26 mg) is obtained by preparative RP-HPLC.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in acetic acid (2 ml)
  4. additioniron (115 mg; powder) is added
  5. filtrationThe mixture is filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d097c8bfece94fa68103dd114a4be032
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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