Dimethylformamide → HCID 23362212, compound

HRID 1082115Notes

Reaction equation

HRID 1082115 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22](Br)[C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=1)[CH3:11].[C:28]([O-:31])(=[S:30])[CH3:29].[K+].CN(C)C=O>O>[C:28]([S:30][CH:22]([CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][N:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH3:11])=[CH:16][CH:17]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:31])[CH3:29]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 23362208HCID 23362208, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 23362212HCID 23362212, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-bromopropanoate (1.25 g), potassium thioacetate (0.5 g) and dry N,N-dimethylformamide (15 mL) was heated at 80° C. for 18 hours under a nitrogen atmosphere. The mixture was diluted with water (1 L) and extracted with ethyl acetate (3×250 mL). The combined ethyl acetate solutions were washed with water (3×250 mL) and brine (500 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 40% ethyl acetate in hexane as eluent to afford the title compound, a gum.

Workup

  1. extractionextracted with ethyl acetate (3×250 mL)
  2. washThe combined ethyl acetate solutions were washed with water (3×250 mL) and brine (500 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel with 40% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-c248e420e12f49118dde303e75b3bb49
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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