Diethyl Ether → HCID 131722201, compound

HRID 1274581Notes

Reaction equation

HRID 1274581 reaction equation
[CH2:1]([O:3][C:4]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][N:16]=[C:15]([C:18]4[CH:19]=[C:20](C)[C:21](O)=[CH:22][CH:23]=4)[C:14]=3[CH:26]=2)[C:8](=[O:27])[CH:7]=[C:6]([C:28]([F:31])([F:30])[F:29])[N:5]=1)[CH3:2].[C:32](=[O:35])([O-])[O-].[K+].[K+].BrC[C:40](OC)=[O:41].[CH2:44](OCC)C.CN(C)[CH:51]=[O:52]>C(OCC)(=O)C.C(Cl)Cl>[CH3:40][O:41][C:51](=[O:52])[CH2:32][O:35][C:20]1[CH:21]=[CH:22][C:23]([CH3:44])=[C:18]([C:15]2[C:14]3[CH:26]=[C:10]([N:9]4[C:8](=[O:27])[CH:7]=[C:6]([C:28]([F:31])([F:29])[F:30])[N:5]=[C:4]4[O:3][CH2:1][CH3:2])[CH:11]=[CH:12][C:13]=3[S:17][N:16]=2)[CH:19]=1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 136333722HCID 136333722, compound

Product 1

HCID 131722201HCID 131722201, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-ethoxy-3-[3-(6-hydroxy-m-tolyl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)-4(3H)-pyrimidinone (0.470 g, 1.05 mmol), potassium carbonate (0.190 g, 1.37 mmol) and methyl bromoacetate (0.210 g, 1.37 mmol) in N,N-dimethylformamide is stirred overnight at room temperature, diluted with ethyl acetate, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Flash column chromatography of the solid using silica gel and a 10% diethyl ether in methylene chloride solution gives the title product as an off-white solid (0.450 g, mp 171-174° C.).

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a solid

Sources & evidence

ORD record
ord-e280f0c0908e4dd59b2cd20a6bbdda23
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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