Pyridine → 2-Thiophen-2-ylacetic acid benzyl-(4-bromo-2-chlorobenzyl)amide

HRID 840646Notes

Reaction equation

HRID 840646 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][C:30](Cl)=[O:31]>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[Cl:17])[C:30](=[O:31])[CH2:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1623622-Thiopheneacetyl chlorideHCID 22619993Benzyl-(4-bromo-2-chlorobenzyl)amine

Product 1

HCID 701720702-Thiophen-2-ylacetic acid benzyl-(4-bromo-2-chlorobenzyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

580 mg of benzyl-(4-bromo-2-chlorobenzyl)amine are dissolved in 10 ml of CH2Cl2 (anhydrous) and treated first with 300 μl of pyridine, then with 330 mg of 2-thiophen-2-ylacetyl chloride. The mixture is stirred at RT for 4 h, then diluted with 100 ml of CH2Cl2 and washed with 50 ml of a saturated aqueous Na2CO3 solution. It is dried over MgSO4 and the solvent is removed in vacuo. It is chromatographed on silica gel using DIP and 490 mg of a colorless oil are obtained.

Workup

  1. washwashed with 50 ml of a saturated aqueous Na2CO3 solution
  2. dry with materialIt is dried over MgSO4
  3. customthe solvent is removed in vacuo
  4. customIt is chromatographed on silica gel using DIP and 490 mg of a colorless oil
  5. customare obtained

Sources & evidence

ORD record
ord-0ad3cdf1057941d391edd2375d7ac0fb
Source dataset
uspto-grants-2002_04
Patent number
US06369069B1

Reaction notes

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