Furfurylamine → 4-chloro-N-(furan-2-ylmethyl)benzamide

HRID 906646Notes

Reaction equation

HRID 906646 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH:11]1[CH:15]=[C:14]([CH2:16][NH2:17])[O:13][CH:12]=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:17][CH2:16][C:14]2[O:13][CH:12]=[CH:11][CH:15]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3438FurfurylamineHCID 85014-Chlorobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 7201384-chloro-N-(furan-2-ylmethyl)benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-chlorobenzoyl chloride (3.2 g, 18.5 mol) in 50 ml dry CH2Cl2 was added over 30 min to a stirred solution of 2-furfurylamine (2 g, 20.6 mol) and iPr2NEt (7 ml, 41 mol) in CH2Cl2 (200 ml) at 0° C. The reaction was allowed to warm to room temperature over 3 h. The mixture was diluted with 200 ml of CH2Cl2, washed twice with HCl aq. (1N) and dried over MgSO4. Evaporation of the solvent afforded 4 g (83%) of the title benzamide as a white solid: 1H NMR: (DMSO-d6) δ 9.05 (t, J=5.7 Hz, 1H), 7.89 (d, J=8.7 Hz, 2H), 7.57 (m, 1H), 7.53 (d, J=8.7 Hz, 2H), 6.40 (dd, J=3.7, 1.1 Hz, 1H), 6.28 (d, J=3.7 Hz, 1H), 4.46 (d, J=5.6 Hz, 2H). M/Z APCI: 236.6 (M+1), 234.8 (M−1).

Workup

  1. washwashed twice with HCl aq. (1N)
  2. dry with materialdried over MgSO4
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ada74e7d8f3741fa8e4c8ea3e82d1813
Source dataset
uspto-grants-2011_09
Patent number
US08012995B1

Reaction notes

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