P-Anisidine → HCID 178443034, compound

HRID 1833522Notes

Reaction equation

HRID 1833522 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.[CH3:48][O:49][C:50]1[CH:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=1>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:56][C:53]1[CH:54]=[CH:55][C:50]([O:49][CH3:48])=[CH:51][CH:52]=1)=[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

4

Reactant 2

HCID 7732P-AnisidineHCID 12565115Ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-thiobenzimidate Dihydrochloride

Product 1

HCID 178443034HCID 178443034, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ethyl-m-[N,N-di(n-hexadecyl)aminomethyl]-thiobenzimidate dihydrochloride (1.074 g., 1.5 mmoles), p-anisidine (369 mg., 3.0 mmoles) and chloroform (10 ml.) was held at room temperature for sixteen hours. It was then diluted to 400 ml. with chloroform, washed with 1N HCl (2 × 50 ml.), dried (Na2SO4) and evaporated in vacuo to a foam. The foam was crystallized from 1,2-dimethoxyethane [868 mg., 73% yield, Rf 0.64 (4:1, benzene:ethanol on silicic acid), m.p.-forms a gel at 84°-86° C⟧

Workup

  1. waitwas held at room temperature for sixteen hours
  2. additionIt was then diluted to 400 ml
  3. washwith chloroform, washed with 1N HCl (2 × 50 ml.)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo to a foam
  6. customThe foam was crystallized from 1,2-dimethoxyethane [868 mg
  7. customat 84°-86° C

Sources & evidence

ORD record
ord-06d4a62338e447bf880329d3bac1a3f2
Source dataset
uspto-grants-1978_01
Patent number
US04066696

Reaction notes

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