Ethanol → 9-chloro-7-(2-chlorophenyl)-2-(methylthio)-5H-pyrimido[5,4-d][2]benzazepine

HRID 464175Notes

Reaction equation

HRID 464175 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:21]=[C:20]([SH:22])[N:19]=[CH:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.S(OC)(O[CH3:29])(=O)=O.[OH-].[Na+].C(O)C>O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:21]=[C:20]([S:22][CH3:29])[N:19]=[CH:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 1785278489-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-2-thiol

Product 1

HCID 132255139-chloro-7-(2-chlorophenyl)-2-(methylthio)-5H-pyrimido[5,4-d][2]benzazepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.1 g (3.0 mmole) of 9-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-thiol, 1.0 ml (10 mmole) of dimethyl sulfate, 20 ml of 1N sodium hydroxide and 10 ml of ethanol was stirred at room temperature for 15 min. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give an oil. Crystallization from ether gave colorless prisms, mp 187°-188° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customto give an oil
  5. customCrystallization from ether
  6. customgave colorless prisms, mp 187°-188° C.

Sources & evidence

ORD record
ord-8afc0dedf7794f6d9ba1395a2f02990a
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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