Ammonium Chloride → HCID 18551247, compound

HRID 1698835Notes

Reaction equation

HRID 1698835 reaction equation
[CH3:1][C:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH2:3][C:4](=[O:20])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[O:17])[O:15][N:14]=[C:13]([CH3:18])[C:12]=2[CH:19]=1)=[O:6].[CH3:28][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[OH:20][C:4]([CH3:28])([CH2:3][C:2]([CH3:1])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH3:21])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[O:17])[O:15][N:14]=[C:13]([CH3:18])[C:12]=2[CH:19]=1)=[O:6]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18551238HCID 18551238, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18551247HCID 18551247, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

72 mg of 6-(4-methyl4-phenyl-2-oxo-valeroylamino)-4-methyl-2,3-benzoxazin-1-one in 4 ml of tetrahydrofuran is mixed with 3 ml of methylmagnesium bromide (3 mol) at 0° C. After 30 minutes, ammonium chloride solution is added, the organic phase is separated, dried and concentrated by evaporation. After chromatography on silica gel (hexane/ethyl acetate 1:1), 39 mg of 6-(2-hydroxy-2,4-dimethyl4-phenyl-valeroylamino)-4-methyl-2,3-benzoxazin-1-one, melting point 173-175° C., is obtained.

Workup

  1. customthe organic phase is separated
  2. customdried
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5cb43b846afe489eb97455e5f24744c5
Source dataset
uspto-grants-2002_02
Patent number
US06344454B1

Reaction notes

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