2-Tolyl isocyanate → HCID 19607763, compound

HRID 745071Notes

Reaction equation

HRID 745071 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30]>ClCCl>[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29]([NH:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1)=[O:30]

Participants

4

Reactant 2

HCID 691942-Tolyl isocyanateHCID 10587836(4-aminophenyl)-(2,3,4,5-tetrahydro-1-benzazepin-1-yl)methanone

Product 1

HCID 19607763HCID 19607763, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.06 g) in dichloromethane (80 ml) is added o-methylphenyl isocyanate (0.66 g) under ice-cooling. The mixture is stirred at room temperature for 4 hours. After completion of the reaction, the solvent is concentrated under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1), and recrystallized from ethyl acetate to give 1-[4-(2-methylanilinocarbonylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.97 g) as white powder, m.p. 182°-182.5° C.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. concentrationthe solvent is concentrated under reduced pressure
  4. customthe resulting residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e5d0ae83af6c4a9783183611733fe683
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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