Hydrogen Peroxide → HCID 14835381, compound

HRID 1199006Notes

Reaction equation

HRID 1199006 reaction equation
OO.[NH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)=[O:13]>C(O)(=O)C>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[O:13][N:3]=[C:4]3[C:9]([CH3:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=23)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 14835380HCID 14835380, compound

Product 1

HCID 14835381HCID 14835381, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
95 °C

Procedure

A solution of 130 ml of 30% hydrogen peroxide in 350 ml of glacial acetic acid was heated on a steam bath for 1 hr and then cooled. To the cooled solution was added 31.0 g (0.0955 mole) of (2-amino-5-chloro-3-methylphenyl)(4-bromophenyl)methanone followed by 450 ml of glacial acetic acid. The reaction mixture was heated to 95° C. to dissolve all solids, heated at 65°-70° C. for 8 hr and then cooled. The reaction mixture was poured into 2.5 liters of ice water and let stand at ambient temperature for 3 hr and filtered. The filter cake was washed with 500 ml of 10% sodium bicarbonate solution and 500 ml of water and dried to give 22.5 g of solid. The solid was recrystallized from 2-propanol to give 20.5 g (67%) of fluffy yellow needles, m.p. 163°-165° C.

Workup

  1. temperaturecooled
  2. dissolutionto dissolve all solids
  3. temperatureheated at 65°-70° C. for 8 hr
  4. temperaturecooled
  5. filtrationfiltered
  6. washThe filter cake was washed with 500 ml of 10% sodium bicarbonate solution and 500 ml of water
  7. customdried

Sources & evidence

ORD record
ord-1b129727e23140a791b3993332bd4f87
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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