Diethylamine → HCID 23332767, compound

HRID 224342Notes

Reaction equation

HRID 224342 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[C:13]2[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[CH:16][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]1=[O:23].[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25]>CN(C)C=O>[ClH:1].[CH2:24]([N:26]([CH2:27][CH3:28])[CH2:2][CH2:3][N:4]1[C:13]2[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[CH:16][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]1=[O:23])[CH3:25]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 23332731HCID 23332731, compound

Product 1

HCID 23332767HCID 23332767, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Four grams (0.0123 mole) of the compound of Example 27, 3.81 ml (0.0369 mole) of diethylamine and 80 ml of dimethylformamide were heated at 80° C. for 6 hours. After evaporating the solvent, the reaction mass was taken up with chloroform, and the obtained organic solution was first washed with a saturated aqueous solution of sodium carbonate and then with water (twice). After drying over sodium sulfate, the chloroform was evaporated off and the obtained residue was passed through a silica-gel column by eluting with chloroform:methanol=99:1 (by volume). The obtained product was finally dissolved in diethyl ether and treated with a saturated solution of hydrogen chloride in diethyl ether whereby the title compound crystallized out. Yield 3.7 g. (76%). M.p. 252°-56° C.

Workup

  1. customAfter evaporating the solvent
  2. washthe obtained organic solution was first washed with a saturated aqueous solution of sodium carbonate
  3. dry with materialAfter drying over sodium sulfate
  4. customthe chloroform was evaporated off
  5. washby eluting with chloroform
  6. dissolutionThe obtained product was finally dissolved in diethyl ether
  7. additiontreated with a saturated solution of hydrogen chloride in diethyl ether whereby the title compound
  8. customcrystallized out

Sources & evidence

ORD record
ord-c5c99d168c7c44b3a44d86fd601bc8bf
Source dataset
uspto-grants-1980_11
Patent number
US04232017

Reaction notes

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