Ammonia → m-[N,N-Di-(n-hexadecyl)aminomethyl]-benzamidine

HRID 2398839Notes

Reaction equation

HRID 2398839 reaction equation
Cl.Cl.C(O[C:6](=[NH:47])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:15]CCCCCCCCCCCCCCC)[CH:8]=1)C.[NH3:48]>C(O)C>[CH2:31]([N:14]([CH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([NH2:47])=[NH:48])[CH2:15][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH3:31])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 70618744Ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-benzimidate dihydrochloride

Product 1

HCID 54256386m-[N,N-Di-(n-hexadecyl)aminomethyl]-benzamidineYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-benzimidate dihydrochloride (35.0 g., 0.05 mole) was dissolved in ethanol (150 ml.) and the mixture saturated with ammonia gas at 20° C. The mixture was held for three hours at 20° C., resaturated with ammonia gas at 20° C., and then stoppered and held overnight at room temperature. The mixture was evaporated in vacuo to a solid which was triturated with acetone (200 ml.), filtered, washed with water (4 × 100 ml.), triturated again with acetone (2 × 100 ml.), filtered and dried in vacuo overnight [22.0 g., 74% yield, Rf 0.42 (4:1, benzene-ethanol on silicic acid)]. The crude product was recrystallized from hot acetone (20.9 g., 70% yield, m.p.-forms a gel at 84° C.).

Workup

  1. customat 20° C
  2. waitheld overnight at room temperature
  3. customThe mixture was evaporated in vacuo to a solid which
  4. customwas triturated with acetone (200 ml.)
  5. filtrationfiltered
  6. washwashed with water (4 × 100 ml.)
  7. customtriturated again with acetone (2 × 100 ml.)
  8. filtrationfiltered
  9. dry with materialdried in vacuo overnight [22.0 g., 74% yield, Rf 0.42 (4:1, benzene-ethanol on silicic acid)]
  10. customThe crude product was recrystallized from hot acetone (20.9 g
  11. customat 84° C.

Sources & evidence

ORD record
ord-be9570f10b1644e6a3b33e63966b0662
Source dataset
uspto-grants-1977_05
Patent number
US04025555

Reaction notes

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