Water → HCID 67693096, compound

HRID 863887Notes

Reaction equation

HRID 863887 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. Calcd for C25H24NSClO2 : C=68.56, H=5.52, N=3.20, Cl=8.09, S=7.32 Found C=68.33, H=5.50, N=3.16, Cl=8.18, S=7.32

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-f9fd3c022b1e4551be9a0d8a2ed48b4d
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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