Pyridine → N-(3-Iodophenyl)-4-(tetradecyloxy)benzeneacetamide

HRID 483590Notes

Reaction equation

HRID 483590 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[CH2:15]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37](Cl)=[O:38])=[CH:32][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:37](=[O:38])[CH2:36][C:33]2[CH:34]=[CH:35][C:30]([O:29][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][CH3:28])=[CH:31][CH:32]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 122713-IodoanilineHCID 10021844p-Tetradecyloxyphenylacetylchloride

Product 1

HCID 15030163N-(3-Iodophenyl)-4-(tetradecyloxy)benzeneacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 14.29 g of m-iodoaniline and 15.52 g of pyridine in 150 ml of tetrahydrofuran is added at room temperature over 20 minutes a solution of p-tetradecyloxyphenylacetyl chloride in 150 ml of tetrahydrofuran. The mixture is stirred overnight and the solvent removed. The residue is partitioned between dilute hydrochloric acid and warm chloroform. The separated organic layer is washed with dilute hydrochloric acid, dried and evaporated to a residue which is crystallized from carbon tetrachloride:hexane to give 25.0 g of the desired product as a pink solid, m.p. 108°-110° C.

Workup

  1. customthe solvent removed
  2. customThe residue is partitioned between dilute hydrochloric acid
  3. temperaturewarm chloroform
  4. washThe separated organic layer is washed with dilute hydrochloric acid
  5. customdried
  6. customevaporated to a residue which
  7. customis crystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-dc18c48e849b43ceaa3bb892b12a74a0
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Reaction notes

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