Triethylamine → 2-(4-Chlorobenzoylamino)-4,5-dimethoxybenzamide

HRID 2408995Notes

Reaction equation

HRID 2408995 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>C1COCC1>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:1][C:2]2[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])=[O:28])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 108672362-Amino-4,5-dimethoxybenzamide

Product 1

HCID 229974052-(4-Chlorobenzoylamino)-4,5-dimethoxybenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-4,5-dimethoxybenzamide (2.0 g, 10.47 mmol) in THF (15 mL) and triethyl amine (3 mL, 20.91 mol) was added solution of 4-chlorobenzoyl chloride (2.2 g, 12.57 mol) in THF (5.0 mL) at rt for 10 min. The reaction mixture was stirred at rt 16 h. The solution was poured into ice cold water and stirred for 10 min. The separated solid was filtered, washed with ice cold water and dried to the product as a pale yellow color solid (2.9 g, 85%), mp 120-122° C. 1H NMR (400 MHz, DMSO-d6): δ 13.38 (1H, s), 8.48 (1H, br s), 8.33 (1H, br s), 7.94 (2H, d, J=8.0 Hz), 7.66 (1H, s), 7.65 (2H, d, J=8.0 Hz), 7.46 (1H, s), 3.84 (3H, s), 3.81 (3H, s); LC-MS (negative ion mode): m/z 333, 335 (M−H)−.

Workup

  1. additionThe solution was poured into ice cold water
  2. stirringstirred for 10 min
  3. filtrationThe separated solid was filtered
  4. washwashed with ice cold water
  5. dry with materialdried to the product as a pale yellow color solid (2.9 g, 85%), mp 120-122° C

Sources & evidence

ORD record
ord-f4e43120a76848a9bfaf581bb52766cf
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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