N-Hydroxyphthalimide → N-(4-nitro-2-trifluoromethyl-phenoxy)-phthalimide

HRID 2292260

Reaction equation

HRID 2292260 reaction equation
[H-].[Na+].[OH:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[N+:15]([C:18]1[CH:23]=[CH:22][C:21](Cl)=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1)([O-:17])=[O:16]>>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:3][N:4]2[C:5](=[O:14])[C:6]3=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]3[C:8]2=[O:9])=[C:20]([C:25]([F:26])([F:27])[F:28])[CH:19]=1)([O-:17])=[O:16]

Participants

4

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 24758Sodium hydrideHCID 612132-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 21277347N-(4-nitro-2-trifluoromethyl-phenoxy)-phthalimideYield 77.7%

Conditions

Temperature
20 °C

Procedure

11.5 g of sodium hydride as a 50% oil suspension were admixed at 20° C. with 300 ml of anhydrous diemthylformamide and after cooling the mixture to 5° to 10° C., 36.5 g of N-hydroxy-phthalimide were added thereto. The mixture was stirred at 20° C. for 30 minutes and 50 g of 4-nitro-2-trifluoromethyl-chloro benzene were added over 10 minutes. The suspension was heated at 80°-85° C. for one hour and was cooled to 20° C. and poured over ice. The mixture was stirred for one hour and was filtered. The solid product was washed with water and dried to obtain 60.7 g of N-(4-nitro-2-trifluoromethyl-phenoxy)-phthalimide melting at 190° C.

Workup

  1. customwere admixed at 20° C. with 300 ml of anhydrous diemthylformamide
  2. temperatureafter cooling the mixture to 5° to 10° C.
  3. temperatureThe suspension was heated at 80°-85° C. for one hour
  4. temperaturewas cooled to 20° C.
  5. additionpoured over ice
  6. stirringThe mixture was stirred for one hour
  7. filtrationwas filtered
  8. washThe solid product was washed with water
  9. customdried

Sources & evidence

ORD record
ord-a77c0d20f75e477db6b4fee4f73d3b13
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Linked notes

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