Thionyl Chloride → HCID 19107605, compound

HRID 1197645Notes

Reaction equation

HRID 1197645 reaction equation
S(Cl)(Cl)=O.O[C:6]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[CH2:7][C:8]#[N:9]>N1C=CC=CC=1>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[CH:7][C:8]#[N:9])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19107597HCID 19107597, compound

Product 1

HCID 19107605HCID 19107605, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thionyl chloride (2.18 g, 0.018 mol) was slowly added to a stirred solution of 3-hydroxy-3,3-di(4-methoxyphenyl)propanenitrile (4.0 g, 0.014 mol) in pyridine (30 ml) cooled in an ice-salt bath. After the addition was complete the mixture was allowed to warm up to room temperature and stirred for 2 h. ice cold water (100 ml) was added and the mixture extracted with DCM (2×100 ml) The combined organics were washed with 3M hydrochloric acid (1×50 ml, 1×5 ml) , brine (50 ml) , dried over anhydrous sodium sulphate, filtered and evaporated to yield crude 3,3-di(4-methoxyphenyl)-2-propenenitrile (2.95 g, 79%) which was used directly in the next step.

Workup

  1. temperaturecooled in an ice-salt bath
  2. additionAfter the addition
  3. additionwas added
  4. extractionthe mixture extracted with DCM (2×100 ml) The combined
  5. washorganics were washed with 3M hydrochloric acid (1×50 ml, 1×5 ml) , brine (50 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-2c5800f4c00c4d25b165233d4bef44e2
Source dataset
uspto-grants-1994_01
Patent number
US05276153

Reaction notes

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