Water → HCID 67693096, compound

HRID 273997Notes

Reaction equation

HRID 273997 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]([S:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25]O)[CH:20]=2)[C:16]#[N:17])[CH:10]=[CH:11][C:12]=1OC.O.CN(C)[CH:38]=[O:39]>>[Cl:3][CH2:25][C:21]1[CH:20]=[C:19]([CH2:18][C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[C:8]=2[O:39][CH3:38])([S:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[C:16]#[N:17])[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24386Thionyl ChlorideHCID 10716967HCID 10716967, compound

Product 1

HCID 67693096HCID 67693096, compound

Procedure

A mixture of 0.1 mL of thionyl chloride and 0.12 mL of N,N-dimethyl formamide is stirred at room temperature for 30 minutes. A solution of 0.34 g of α-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-α-[(4-methylphenyl)thio]benzene propane nitrile in 1.0 mL of N,N-dimethylformamide is added to the above mixture and the resulting mixture is heated at 70° C. for 17 hours, cooled, poured into water and extracted with diethyl ether. The diethyl ether extract is washed with brine, dried and filtered. The filtrate is evaporated in vacuo to yield an oil. This oil is purified by flash chromatography using 10% ethyl acetate in hexane to yield 0.27 g of the desired product as a colorless oil.

Workup

  1. temperaturethe resulting mixture is heated at 70° C. for 17 hours
  2. temperaturecooled
  3. extractionextracted with diethyl ether
  4. extractionThe diethyl ether extract
  5. washis washed with brine
  6. customdried
  7. filtrationfiltered
  8. customThe filtrate is evaporated in vacuo
  9. customto yield an oil
  10. customThis oil is purified by flash chromatography

Sources & evidence

ORD record
ord-6ace9bf7ef6346db929470f4d7e5d82a
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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