Chloroacetyl chloride → HCID 178456413, compound

HRID 359936Notes

Reaction equation

HRID 359936 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].C(N(CCCC)CCCC)CCC.Cl[CH2:20][C:21](Cl)=[O:22].[CH2:24]([NH2:27])[CH:25]=[CH2:26]>CN(C=O)C.C(O)(C)C>[CH2:24]([N:27]1[CH2:20][C:21](=[O:22])[C:2]([C:3]#[N:4])=[C:1]1[NH2:5])[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 7622TributylamineHCID 7853AllylamineHCID 8010Malononitrile

Product 1

HCID 178456413HCID 178456413, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

19.8 g of malononitrile were dissolved in 30 ml of DMF and cooled to 0° C. While cooling, 87 g of tributylamine and 27 g of chloroacetyl chloride were simultaneously added dropwise to this, and the mixture was stirred at 10° C. for 10 minutes. The mixture was then added to a mixture of 300 g of ice and 43 g of allylamine and stirred at room temperature for 8 hours. The precipitate was filtered off with suction, washed and dried. 38.1 g (78% of theory) of impure crude product were obtained and were boiled in 150 ml of isopropanol to purify. After cooling to 5° C., the precipitate was filtered off with suction, washed and dried. 31.2 g (64% of theory) of the compound of the formula ##STR26## of melting point 275° to 278° C. were obtained The IR, NMR, UV and mass spectra and the elemental analysis are consistent with the structural formula.

Workup

  1. temperatureWhile cooling
  2. stirringstirred at room temperature for 8 hours
  3. filtrationThe precipitate was filtered off with suction
  4. washwashed
  5. customdried
  6. custom38.1 g (78% of theory) of impure crude product were obtained
  7. customto purify
  8. temperatureAfter cooling to 5° C.
  9. filtrationthe precipitate was filtered off with suction
  10. washwashed
  11. customdried
  12. custom31.2 g (64% of theory) of the compound of the formula ##STR26## of melting point 275° to 278° C. were obtained The IR, NMR, UV and mass spectra

Sources & evidence

ORD record
ord-893a5ca503dd41c393aa27e9695f9c25
Source dataset
uspto-grants-1991_03
Patent number
US05003081

Reaction notes

Loading…