Dimethylformamide → HCID 22472042, compound

HRID 1071222Notes

Reaction equation

HRID 1071222 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.C([S-])C.[Na+].[CH2:26]([N:28](CC)CC)[CH3:27].CN(C)C=O>O>[CH2:26]([NH:28][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 4459711Sodium ethanethiolateHCID 22472049HCID 22472049, compound

Product 1

HCID 22472042HCID 22472042, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-Bromo-6-methoxy-2-(4-methoxyphenyl)-1H-inden-1-one (150 mg, 0.4345 mmol), sodium ethanethiolate (91.4 mg, 1.09 mmol), and triethyl amine (0.5 ml) in N,N, dimethyl formamide (3 mL) was heated at 80° C. for 24 h. The reaction was cooled to room temperature was poured into water and extracted with ethyl acetate. The organic extracts were washed with brine and were dried over MgSO4. Evaporation and flash chromatography (10% ethyl acetate/petroleum ether) gave (126 mg, 89% yield) of the product as a dark red solid: mp 88-90° C.; MS m/e 327 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialwere dried over MgSO4
  5. customEvaporation and flash chromatography (10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-fb62e9ed7a674224bf0e05252b177820
Source dataset
uspto-grants-2005_06
Patent number
US06903238B2

Reaction notes

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