Acetic Acid → HCID 178443033, compound

HRID 1833523Notes

Reaction equation

HRID 1833523 reaction equation
Cl.Cl.C(S[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:8]=1)C.[CH:48]1([NH2:53])[CH2:52][CH2:51][CH2:50][CH2:49]1.C(O)(=O)C>C(Cl)(Cl)Cl>[CH2:31]([N:14]([CH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([NH:53][CH:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1)=[NH:47])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[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

5

Reactant 3

HCID 176Acetic AcidHCID 2906CyclopentylamineHCID 12565115Ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-thiobenzimidate Dihydrochloride

Product 1

HCID 178443033HCID 178443033, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-thiobenzimidate dihydrochloride (1.074 g., 1.5 mmoles) was added to a solution of cyclopentylamine (255 mg., 3.0 mmoles), glacial acetic acid (0.3 ml., 5.3 mmoles) and chloroform (10 ml.). The mixture was held for 72 hours at room temperature. It was then diluted to 300 ml. with chloroform, washed with saturated aqueous sodium bicarbonate solution (3 × 50 ml.), washed with saturated aqueous sodium chloride solution (3 × 50 ml.), dried (Na2SO4) and filtered. The filtrate was acidified with a 10% solution of anhydrous hydrogen chloride in dioxane (5 ml.) and then evaporated in vacuo to an oil. The oil was crystallized from warm 1,2-dimethoxyethane [850 mg., 77% yield, Rf 0.30 (4:1, benzene:ethanol on silicic acid), m.p.-forms a gel at 78° C⟧

Workup

  1. additionIt was then diluted to 300 ml
  2. washwith chloroform, washed with saturated aqueous sodium bicarbonate solution (3 × 50 ml.)
  3. washwashed with saturated aqueous sodium chloride solution (3 × 50 ml.)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil
  7. customThe oil was crystallized
  8. temperaturefrom warm 1,2-dimethoxyethane [850 mg
  9. customat 78° C

Sources & evidence

ORD record
ord-2b435d73dd0d4310a79e2d1e52ab56e4
Source dataset
uspto-grants-1978_01
Patent number
US04066696

Reaction notes

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