Sodium Hydroxide → HCID 13655355, compound

HRID 745271Notes

Reaction equation

HRID 745271 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[OH-].[Na+].Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 805662,4-DichlorophenylacetonitrileHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 13655355HCID 13655355, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 18.5 parts of 2,4-dichlorobenzeneacetonitrile and 180 parts of N,N-dimethylformamide is stirred and cooled in an ice-bath while nitrogen gas is introduced. 3.2 Parts of a sodium hydroxide solution 78% are added portionwise and the whole is stirred for one hour. Then there are added dropwise, during a one hour-period, 17.8 parts of (bromomethyl)cyclohexane while still cooling and while nitrogen gas is still introduced. Upon completion, stirring is continued for 2 hours at room temperature. The reaction mixture is poured onto water. The precipitated product is filtered off and triturated in a mixture of methanol and water. The product is filtered off and dried, yielding 25.5 parts of 2,4-dichloro-α-(cyclohexylmethyl)benzeneacetonitrile; mp. 58.8° C.

Workup

  1. temperaturecooled in an ice-bath while nitrogen gas
  2. additionis introduced
  3. stirringthe whole is stirred for one hour
  4. temperaturewhile still cooling and while nitrogen gas
  5. additionis still introduced
  6. stirringUpon completion, stirring
  7. additionThe reaction mixture is poured onto water
  8. filtrationThe precipitated product is filtered off
  9. customtriturated in a mixture of methanol and water
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-c2d8cbe2136342b0b26a3ce2167930ec
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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