N′-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]-N,N-dimethylurea → Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one

HRID 1735021Notes

Reaction equation

HRID 1735021 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](N(C)C)=[O:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C(OC(=O)C)(=O)C>[CH2:2]1[N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][C:8]=3[C:17](=[O:18])[NH:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=32)[CH2:3]1

Participants

3

Reactant 1

HCID 15380027N′-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]-N,N-dimethylurea

Product 1

HCID 15380028Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

N-[2-(Indolin-1-yl)phenyl]-dimethylaminocarboxamide (37 gm; 0.13 moles) in acetic anhydride (140 ml) was refluxed for 30 minutes. The mixture was cooled to ~50° C., and thereafter concentrated on a rotary evaporator to about 80 ml while crystallization occurred. The red solid was filtered and washed with ether. Recrystallization from chloroform (500 ml) afforded red-orange crystals: 21.3 gm (68%), m.p. 213.5°-214.5° C.

Workup

  1. temperatureThe mixture was cooled to ~50° C.
  2. concentrationconcentrated on a rotary evaporator to about 80 ml while crystallization
  3. filtrationThe red solid was filtered
  4. washwashed with ether
  5. customRecrystallization from chloroform (500 ml)
  6. customafforded red-orange crystals

Sources & evidence

ORD record
ord-49c49b3eeb7845f5b40464386b8a6417
Source dataset
uspto-grants-1996_07
Patent number
US05536717

Reaction notes

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