4-Chlorobenzoyl chloride → 4-chloro-N-(thiophen-2-ylmethyl)benzamide

HRID 2113729Notes

Reaction equation

HRID 2113729 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 34005(2-Thienylmethyl)amineHCID 81531Diisopropylethylamine

Product 1

HCID 7222864-chloro-N-(thiophen-2-ylmethyl)benzamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-chlorobenzoyl chloride (0.114 mol) in 50 ml dry CH2Cl2 is added over 30 min to a stirred solution of 2-aminomethylthiophene (0.137 mol) and iPr2NEt (0.25 mol) in CH2Cl2 (200 ml) at 0° C. A white solid is formed and the reaction is allowed to warm to room temperature over 1 h. The mixture is diluted with 200 ml of CH2Cl2, washed twice with HCl aq. (0.1N) and dried over MgSO4. Evaporation of the solvents afforded 28 g (98%) of the title benzamide as a white solid: mp 153-54° C., 1H NMR (CDCl3) δ 7.9 (d, J=8.67 Hz, 2H), 7.58 (d, J=8.67 Hz, 2H), 7.44 (dd, J=3.77, 1.13 Hz, 1H), 7.22 (d, J=5.27 Hz, 1H), 7.16 (dd, J=3.39, 5.27 Hz, 1H), 6.62 (br d, 1H), 4.98 (d, J=5.65 Hz, 2H).

Workup

  1. customA white solid is formed
  2. washwashed twice with HCl aq. (0.1N)
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvents

Sources & evidence

ORD record
ord-5d1981f949964e43a1f5e11a236228b0
Source dataset
uspto-grants-2008_10
Patent number
US07432286B1

Reaction notes

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