O-Cresol → HCID 19607886, compound

HRID 1603104Notes

Reaction equation

HRID 1603104 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[CH2:12][C:13]([NH:15][C:16]1[CH:34]=[CH:33][C:19]([C:20]([N:22]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)=[O:14]>CS(C)=O>[CH3:8][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[O:7][CH2:12][C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([N:22]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])=[CH:33][CH:34]=1)=[O:14]

Participants

5

Reactant 3

HCID 335O-CresolHCID 14798Sodium HydroxideHCID 19608248HCID 19608248, compound

Product 1

HCID 19607886HCID 19607886, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

o-Cresol (0.36 g) is dissolved in dimethylsulfoxide (4 ml) containing sodium hydroxide powder (0.18 g) and thereto is added 1-[4-(2-chloroacetylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.03 g). The mixture is stirred at 90° C. for 7.5 hours. The reaction mixture is poured into ice-water (300 ml) and the precipitated crystal is collected by filtration, washed with water, and purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=2:1), and recrystallized from ethyl acetate to give 1-{4-[2-(2-methylphenoxy)acetylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (546 mg) as colorless scales, m.p. 172.5-175° C.

Workup

  1. filtrationthe precipitated crystal is collected by filtration
  2. washwashed with water
  3. custompurified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=2:1)
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7ae3614a6345407a895ed2ff26be545b
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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