Phenyl isocyanate → HCID 15034987, compound

HRID 1090227Notes

Reaction equation

HRID 1090227 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:16]4[C:17]=3[C:12](=[CH:13][CH:14]=[CH:15]4)[N:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.Cl.N1(CCCNC2C3C=CC=C4C=3C(=CC=C4)N=2)C=CN=C1.[C:45]1([N:51]=[C:52]=[O:53])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>ClCCl>[N:11]1[C:12]2[C:17]3[C:16](=[CH:21][CH:20]=[CH:19][C:18]=3[C:10]=1[N:9]([CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:52]([NH:51][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:53])[CH:15]=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 178419797HCID 178419797, compoundHCID 178478518HCID 178478518, compound

Product 1

HCID 15034987HCID 15034987, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.7 g of N-(3-(1H-imidazol-1-yl)propyl)benz(cd)indol-2-amine (free base of the compound of Example 1) was dissolved in 50 ml of dichloromethane, and the solution then treated with 2.4 grams of phenylisocyanate. The mixture was stirred at room temperature overnight and then washed with 50 ml of saturated NaCHO3 solution. The dichloromethane layer was dried over MgSO4. Removal of the dichloromethane in vacuo left 3.7 grams of the desired compound, melting at 240° C.-250° C. with decomposition.

Workup

  1. washwashed with 50 ml of saturated NaCHO3 solution
  2. dry with materialThe dichloromethane layer was dried over MgSO4
  3. customRemoval of the dichloromethane in vacuo
  4. waitleft 3.7 grams of the desired compound, melting at 240° C.-250° C. with decomposition

Sources & evidence

ORD record
ord-1b51d1f67a9045118c7f9d4970097e48
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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