Methylamine → HCID 19591364, compound

HRID 1601892Notes

Reaction equation

HRID 1601892 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.[C:11]([Si](C)(C)C)#[N:12].[CH3:17][NH2:18]>CCO.[I-].[Zn+2].[I-]>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([NH:12][CH3:11])[C:17]#[N:18])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 227103,4-DichlorobenzaldehydeHCID 82115Trimethylsilyl cyanide

Product 1

HCID 19591364HCID 19591364, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10 g of 3,4-dichlorobenzaldehyde and 9.5 ml of cyanotrimethylsilane is cooled in an ice bath, 10 mg of zinc iodide are added and the mixture is stirred for 30 minutes at RT. 20 ml of a 33% solution of methylamine in EtOH are then added and the mixture is heated at 40° C. for 2 hours. The solvent is concentrated under vacuum, the residue is extracted with ether and the organic phase is dried over MgSO4 and filtered. A saturated solution of gaseous HCl in ether is added to the filtrate until the pH is 1, and acetone is then added until the product precipitates. The precipitate formed is wrung, washed with ether and dried to give 12.8 g of the expected product. M.p.=172° C.

Workup

  1. temperatureis cooled in an ice bath
  2. temperaturethe mixture is heated at 40° C. for 2 hours
  3. concentrationThe solvent is concentrated under vacuum
  4. extractionthe residue is extracted with ether
  5. dry with materialthe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. additionA saturated solution of gaseous HCl in ether is added to the filtrate until the pH is 1, and acetone
  8. additionis then added until the product
  9. customprecipitates
  10. customThe precipitate formed
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-f1df586821b74487bdcf86f80e35bea6
Source dataset
uspto-grants-1999_11
Patent number
US05977359

Reaction notes

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