Isopropanol → HCID 14574097, compound

HRID 893812Notes

Reaction equation

HRID 893812 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:14][NH:15][CH2:16][CH2:17][OH:18].C(O)(C)C.[OH-].[K+]>O>[OH:18][CH2:17][CH2:16][N:15]([CH3:14])[C:4](=[O:5])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[Cl:1].[N+:11]([C:8]1[CH:9]=[CH:10][C:2]2[O:18][CH2:17][CH2:16][N:15]([CH3:14])[C:4](=[O:5])[C:3]=2[CH:7]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 80162-(Methylamino)ethanolHCID 14797Potassium HydroxideHCID 117637Benzoyl chloride, 2-chloro-5-nitro-

Product 2

HCID 14574097HCID 14574097, compoundHCID 14574098HCID 14574098, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

260 g of N-(2-hydroxyethyl)-N-methyl-2-chloro-5-nitrobenzamide, which is prepared from 2-chloro-5-nitrobenzoyl chloride and 2-(methylamino)-ethanol, are heated to reflux temperature in 500 ml of water/500 ml of isopropanol. A solution of 65 g of potassium hydroxide in 250 ml of water is added dropwise in the course of one hour and the mixture is maintained at reflux temperature for a further 3 hours. The pH is lowered to 9, the reaction solution is cooled to 0° C. and the crystalline precipitate is filtered off with suction and dried. 174 g of 7-nitro-4-methyl -2,3-dihydro-1,4-benzoxazepin-5-one of melting point 116° C. are obtained. ##STR21##

Workup

  1. temperatureare heated
  2. temperaturethe mixture is maintained
  3. temperatureat reflux temperature for a further 3 hours
  4. filtrationthe crystalline precipitate is filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-70e22091586d42468620912030a17722
Source dataset
uspto-grants-1992_06
Patent number
US05126481

Reaction notes

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