Dimethylformamide → HCID 68829403, compound

HRID 1727364Notes

Reaction equation

HRID 1727364 reaction equation
ClCCOC(=O)N[C:7]1[S:8][C:9]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:11]=1.[CH3:27][C:28](C)([O-:30])C.[K+].C(=O)([O-])O.[Na+].C[N:39](C)[CH:40]=[O:41]>>[CH3:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]([N:39]3[CH2:27][CH2:28][O:30][C:40]3=[O:41])([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=3)[S:8][CH2:7][N:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 534244992-Chloroethyl [4-(3-methylphenyl)-5-(2-methylpyridin-4-yl)-1,3-thiazol-2-yl]carbamate

Product 1

HCID 68829403HCID 68829403, compoundYield 72%

Procedure

To a solution of 2-chloroethyl[4-(3-methylphenyl)-5-(2-methyl-4-pyridyl)-1,3-thiazol-2-yl]carbamate (0.30 g, 0.80 mmol) in N,N-dimethylformamide (3 mL) was added potassium tert-butoxide (0.12 g, 1.1 mmol), and the mixture was stirred at room temperature for 1 hour. An aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to obtain a crystal. This crystal was recrystallized from hexane-ethyl acetate, to obtain a title compound (0.20 g, yield 72%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1)
  6. customto obtain a crystal
  7. customThis crystal was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8823151c173f4fa880f37f5b095792d6
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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