HCID 19865242, compound → HCID 19865243, compound

HRID 1199598Notes

Reaction equation

HRID 1199598 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:15](=[O:16])[CH2:14][N:13]([CH:17]([CH3:19])[CH3:18])[C:12]2=[O:20])=[C:4]([F:21])[CH:3]=1>C(O)(=O)C.O.C(OCC)C.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:21])=[C:5]([N:11]2[C:15](=[O:16])[CH2:14][N:13]([CH:17]([CH3:19])[CH3:18])[C:12]2=[O:20])[CH:6]=1

Participants

6

Reactant 1

HCID 19865242HCID 19865242, compound

Product 1

HCID 19865243HCID 19865243, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of 4.4 g (0.014 mole) of 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-(1-methylethyl)hydantoin in 70 mL of acetic acid and 10 mL of water was added slowly 4.5 g (0.083 mole) of iron powder. The reaction mixture was heated briefly at 50° C, then was cooled to room temperature and was stirred for 0.5 hour. The mixture was diluted with diethyl ether and was filtered through a pad of Celite® filter aid. The filter pad was rinsed with diethyl ether. The filtrate, containing the diethyl ether wash, was transferred to a separatory funnel and was washed with water and an aqueous dilute sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to give 3.0 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-(1-methylethyl)hydantoin.

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationwas filtered through a pad of Celite®
  3. filtrationfilter aid
  4. washThe filter pad was rinsed with diethyl ether
  5. additionThe filtrate, containing the diethyl ether
  6. washwash
  7. customwas transferred to a separatory funnel
  8. washwas washed with water
  9. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-4425b9a4367841aa83748ef7b2a93dc8
Source dataset
uspto-grants-1990_02
Patent number
US04902338

Reaction notes

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