Acetic Acid → HCID 178443033, compound

HRID 839900Notes

Reaction equation

HRID 839900 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 (Na2 SO4) and filtered. The filtrate was acidified with a 10% solution of anhydrous hydrogen chloride in dioxane (5ml.) and then evaporated in vacuo to an oil. The oil was crystallized from warm 1,2-dimethoxyethane [850 mg., 77% yield, Rf .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. customdried (Na2 SO4)
  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-1da25338006e42c7982145c8edd74e69
Source dataset
uspto-grants-1978_06
Patent number
US04097525

Reaction notes

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