Acetaldehyde → 1-Cyanoethyl 4-(hexadecylamino)benzoate

HRID 126943Notes

Reaction equation

HRID 126943 reaction equation
[C-]#N.[K+].[CH:4]([N:7](C(C)C)CC)(C)C.[CH:13](=[O:15])[CH3:14].Cl.[CH2:17]([NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O1CCCC1>[CH2:17]([NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([O:15][CH:13]([C:4]#[N:7])[CH3:14])=[O:39])=[CH:36][CH:35]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 9032Potassium CyanideHCID 81531DiisopropylethylamineHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 234578721-Cyanoethyl 4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1 g. (16.1 m moles) potassium cyanide, 5 ml. diisopropylethylamine and 800 mg. (18.1 m moles) acetaldehyde in 50 ml. tetrahydrofuran is stirred for 2 hours at room temperature. To this solution is added 6.7 g. (16.1 m moles) 4-(hexadecylamino)benzoyl chloride hydrochloride in 50 ml. tetrahydrofuran. After stirring for an additional 2 hours, the solution is diluted with 100 ml. water and extracted with ether. After drying with magnesium sulfate, the ether is evaporated and the residue is crystallized from acetonitrile to yield the title compound.

Workup

  1. additionA mixture of 1 g
  2. additionTo this solution is added 6.7 g
  3. additionthe solution is diluted with 100 ml
  4. extractionwater and extracted with ether
  5. dry with materialAfter drying with magnesium sulfate
  6. customthe ether is evaporated
  7. customthe residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-6bcecfc534544f4aa1add9d0d6c07ded
Source dataset
uspto-grants-1981_03
Patent number
US04254138

Reaction notes

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