Isopropylamine → HCID 178443204, compound

HRID 359935Notes

Reaction equation

HRID 359935 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].Cl[CH2:7][C:8](Cl)=[O:9].[CH2:11]([NH2:24])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N)(C)C>CN(C=O)C.C(N(CC)CC)C>[NH2:4][C:3]1[N:24]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:7][C:8](=[O:9])[C:2]=1[C:1]#[N:5]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 6577Chloroacetyl chlorideHCID 8010MalononitrileHCID 40761Tridecylamine

Product 1

HCID 178443204HCID 178443204, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

19.8 g of malononitrile were dissolved in 30 ml of DMF and cooled to 0° C. While cooling, 61 g of triethylamine and 27 g of chloroacetyl chloride were simultaneously added dropwise to this, and the mixture was stirred at 10° C. for 10 minutes. 65.7 g of tridecylamine were then added dropwise, and the reaction mixture was stirred at room temperature for 48 hours. 300 ml of isopropylamine were then added to the mixture, which was refluxed for 2 hours, 10 g of active carbon were added, and the mixture was filtered hot. After cooling, the precipitate was filtered off with suction, washed and dried at 50° C. 40 g (44% of theory) of the compound of the formula ##STR25## of melting point 214° to 215° 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. stirringthe reaction mixture was stirred at room temperature for 48 hours
  3. temperaturewas refluxed for 2 hours
  4. addition10 g of active carbon were added
  5. filtrationthe mixture was filtered hot
  6. temperatureAfter cooling
  7. filtrationthe precipitate was filtered off with suction
  8. washwashed
  9. customdried at 50° C
  10. custom40 g (44% of theory) of the compound of the formula ##STR25## of melting point 214° to 215° C. were obtained

Sources & evidence

ORD record
ord-4d2a89e19e394fb7bae643ae04a07e93
Source dataset
uspto-grants-1991_03
Patent number
US05003081

Reaction notes

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