Water → HCID 10254925, compound

HRID 2216294Notes

Reaction equation

HRID 2216294 reaction equation
[CH2:1]([C:3]1[C:8]2[CH:9]=[C:10]([NH:13][C:14](=[O:34])[C:15]([OH:33])([C:29]([F:32])([F:31])[F:30])[CH2:16][C:17]([C:20]3[C:28]4[O:27][CH2:26][CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)([CH3:19])[CH3:18])[CH:11]=[CH:12][C:7]=2[C:6](=[O:35])[O:5][N:4]=1)[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O>O1CCOCC1>[CH2:1]([C:3]1[C:8]2[CH:9]=[C:10]([NH:13][C:14](=[O:34])[C:15]([OH:33])([C:29]([F:32])([F:31])[F:30])[CH2:16][C:17]([C:20]3[C:28]4[O:27][CH:26]=[CH:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)([CH3:19])[CH3:18])[CH:11]=[CH:12][C:7]=2[C:6](=[O:35])[O:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21941663HCID 21941663, compound

Product 1

HCID 10254925HCID 10254925, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

930 mg of (±)-4-ethyl-6-[4-(2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-2,3-benzoxazin-1-one and 680 mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone in 90 ml of dioxane are refluxed for 20 hours, mixed with water and suctioned off. After chromatography on silica gel (hexane/ethyl acetate 1.5+1), 810 mg of (±)-4-ethyl-6-[4-(7-benzofuranyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)valeroylamino]-2,3-benzoxazin-1-one is obtained. Flash point 212° C.

Sources & evidence

ORD record
ord-e014f83e598f46bc83ba4b22d428924c
Source dataset
uspto-grants-2006_09
Patent number
US07112584B2

Reaction notes

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