Dimethylformamide → HCID 57966630, compound

HRID 420583Notes

Reaction equation

HRID 420583 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][C:12]([CH2:17][CH2:18]Cl)([CH2:15][CH3:16])[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:22][O:23][C:24](=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([OH:33])[CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH3:22][O:23][C:24](=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][CH2:16][CH2:15][C:12]2([CH2:17][CH3:18])[CH2:11][CH2:10][N:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:21]=[CH:20][C:5]=4[N:6]=3)[CH2:14][CH2:13]2)[CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 57609492HCID 57609492, compoundHCID 57966568HCID 57966568, compound

Product 1

HCID 57966630HCID 57966630, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 6-chloro-2-[4-(2-chloroethyl)-4-ethyl piperidine-1-yl]benzothiazole (150 mg), (4-chloro-3-hydroxyphenyl)acetic acid methyl ester (176 mg), cesium carbonate (285 mg) and dimethylformamide (2 mL) was stirred at 75° C. for 24 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (174 mg). Yield: 79%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-cc0122a64e14412990cbfba8d6a4a4c7
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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