Chloroacetonitrile → HCID 20570498, compound

HRID 1679527Notes

Reaction equation

HRID 1679527 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:25])[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([OH:24])=[CH:9][CH:10]=2)[O:5]1.Cl[CH2:27][C:28]#[N:29]>CN(C)C=O>[C:28]([CH2:27][O:24][C:8]1[CH:7]=[C:6]2[C:11]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[CH:15]=3)[CH2:13][C:4]([CH3:25])([CH3:3])[O:5]2)=[CH:10][CH:9]=1)#[N:29]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 20570489HCID 20570489, compound

Product 1

HCID 20570498HCID 20570498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (0.93g, 80% dispersion in oil) was added to a solution of 2,2-dimethyl-4-(3-trifluoromethylphenyl) chroman-7-ol (containing 1 mole of carbon tetrachloride of crystallisation) (7.5g) in dimethylformamide (25 ml). Chloroacetonitrile (1.76g) was added and the mixture heated at 60° C for 3 hours. The solvent was removed under reduced pressure and the resulting oil was poured into water. The aqueous solution was extracted with ether and the etheeal extracts were dried (MgSO4) and evaporated under reduced pressure to yield an oil. Chromatography on alumina with ether-petrol (40°-60° C), 1:3 as eluate gave the title compound which crystallised on standing.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe resulting oil was poured into water
  3. extractionThe aqueous solution was extracted with ether
  4. dry with materialthe etheeal extracts were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto yield an oil

Sources & evidence

ORD record
ord-2145e69a277c44bbbdcbf95aee7557a0
Source dataset
uspto-grants-1978_03
Patent number
US04080335

Reaction notes

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