Water → HCID 18759277, compound

HRID 1280382Notes

Reaction equation

HRID 1280382 reaction equation
[F:1][C:2]1[C:3]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]([CH3:31])[C:21]2=[O:32])=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:6]([N+:8]([O-])=O)[CH:7]=1.O>C(O)(=O)C.[Fe]>[F:1][C:2]1[C:3]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[N:22]([CH3:31])[C:21]2=[O:32])=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:6]([CH:7]=1)[NH2:8]

Participants

5

Reactant 2

HCID 962WaterHCID 18759320HCID 18759320, compound

Product 1

HCID 18759277HCID 18759277, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of 4.17 g of 5-fluoro-2-(3-methoxyphenoxy)-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene in 10 ml of acetic acid was added dropwise over 20 minutes to a mixture of 4.5 g of iron powder, 10 ml of acetic acid and 1 ml of water. After the addition, the mixture was stirred for 2 hours, filtered through celite and diluted with ethyl acetate. The resultant was washed with water 2 times, the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 3.67 g of 5-fluoro-2-(3-methoxyphenoxy)-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline.

Workup

  1. additionAfter the addition
  2. filtrationfiltered through celite
  3. additiondiluted with ethyl acetate
  4. washThe resultant was washed with water 2 times
  5. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b582d31aa295485e9b0fc23e11fe968a
Source dataset
uspto-grants-2002_09
Patent number
US06451740B2

Reaction notes

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