Acetic Acid → HCID 178443035, compound

HRID 2398842Notes

Reaction equation

HRID 2398842 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.Cl.[F:49][C:50]([F:54])([F:53])[CH2:51][NH2:52].C([O-])(=O)C.[Na+].C(O)(=O)C>C(Cl)(Cl)Cl>[CH2:15]([N:14]([CH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([NH:52][CH2:51][C:50]([F:54])([F:53])[F:49])=[NH:47])[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])[CH2:16][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]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 517045Sodium AcetateHCID 12565115Ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-thiobenzimidate Dihydrochloride

Product 1

HCID 178443035HCID 178443035, compoundYield 86%

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 slurry of 2,2,2-trifluoroethylamine hydrochloride (406 mg., 3.0 mmoles) and anhydrous sodium acetate (246 mmoles) in chloroform (10 ml.) and glacial acetic acid (0.3 ml., 5.3 mmoles). The mixture was held for 12 hours at room temperature. It was then diluted to 300 ml. with chloroform, washed with saturated aqueous sodium bicarbonate solution (2 × 50 ml.), washed with saturated aqueous sodium chloride solution (2 × 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 a foam. The foam was crystallized from 1,2-dimethoxyethane [974 mg., 86% yield, Rf 0.39 (4:1, benzene:ethanol on silicic acid), m.p.-forms a gel at 125°-127° C⟧

Workup

  1. additionIt was then diluted to 300 ml
  2. washwith chloroform, washed with saturated aqueous sodium bicarbonate solution (2 × 50 ml.)
  3. washwashed with saturated aqueous sodium chloride solution (2 × 50 ml.)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo to a foam
  7. customThe foam was crystallized from 1,2-dimethoxyethane [974 mg
  8. customat 125°-127° C

Sources & evidence

ORD record
ord-3c5f8f0d04f248a8a27e1d3f82b0ce62
Source dataset
uspto-grants-1977_05
Patent number
US04025555

Reaction notes

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