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

HRID 2245299Notes

Reaction equation

HRID 2245299 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 was added over 30 min to a stirred solution of 2-aminomethyl-thiophene (0.137 mol) and iPr2NEt (0.25 mol) in CH2Cl2 (200 mL) at 0° C. A white solid was formed and the reaction was allowed to warm to room temperature over 1 h. The mixture was 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 (1a) as a white solid: m.p. 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 was 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-c6fb2614565d4bd5abea52791e417487
Source dataset
uspto-grants-2010_03
Patent number
US07683078B2

Reaction notes

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