Dimethylformamide → HCID 11035529, compound

HRID 1369627Notes

Reaction equation

HRID 1369627 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:13][C:14]([CH3:17])([O-])[CH3:15].[K+].[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:31][N:32](C=O)[CH3:33]>C1COCC1.[Cl-].[Na+].O.O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]3[CH:33]=[N:32][CH:31]=[C:15]4[S:21][C:20]([C:19]([O:23][CH3:24])=[O:22])=[CH:17][C:14]=34)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 16907Methyl ThioglycolateHCID 823151-(p-Hydroxyphenyl)imidazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 11035529HCID 11035529, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Example 17A (0.88 g, 5 mmol) in THF (15 mL) and DMF (5 mL) was treated with 4-(1-imidazolyl)phenol and potassium t-butoxide (1 N in THF, 5.0 mL, 5 mmol) at 70° C. for 4 hours, then cooled to 0° C., added methyl thioglycolate (0.4 mL, 5 mmol) and cesium carbonate (1.62 g, 5 mmol) then refluxed for 1 hour. The reaction was poured into water, diluted with brine and extracted with ethyl acetate. The ethyl acetate was then washed with 1 N NaOH (2×20 mL), then brine (3×20 mL), dried (MgSO4) to give the titled compound.

Workup

  1. temperaturethen refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was then washed with 1 N NaOH (2×20 mL)
  4. dry with materialbrine (3×20 mL), dried (MgSO4)

Sources & evidence

ORD record
ord-eafaaeed470b46a6bccd76e89ca96db7
Source dataset
uspto-grants-2003_06
Patent number
US06579882B2

Reaction notes

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