Diethylamine → N,N-Diethyl-4-(3-methoxybenzoyl)benzamide

HRID 1912341Notes

Reaction equation

HRID 1912341 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)=[O:7].C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH2:42]([NH:44][CH2:45][CH3:46])[CH3:43]>C(Cl)Cl>[CH2:42]([N:44]([CH2:45][CH3:46])[C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([C:6](=[O:7])[C:5]2[CH:17]=[CH:18][CH:19]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:16][CH:15]=1)[CH3:43]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 100609474-(3-methoxybenzoyl)benzoic Acid

Product 1

HCID 9995598N,N-Diethyl-4-(3-methoxybenzoyl)benzamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.23 grams of acid (3.1b), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.2 equivalents with respect to the acid) and 1-hydroxy benzotriazol hydrate (1.2 equivalents) in anhydrous CH2Cl2 (2 ml) is stirred at room temperature for 30 minutes. A solution of diethylamine (1.5 equivalents) in anhydrous CH2Cl2 (8 ml) is then dropwise added. The obtained mixture is stirred at room temperature for 14 hours and washed in a first step with saturated aqueous sodium bicarbonate and in a second step with water. The organic phase is dehydrated with sodium sulphate, filtered and evaporated under vacuum. The residue that is recovered is purified by flash chromatography (ligroin/ethyl acetate 1/1 v/v). N,N-diethyl-4-(3′-methoxybenzoyl)benzamide (3.1c) is obtained. Yield: 98%. IR (nujol) (λ=cm−1) 1690 (C═O); 1H-NMR (CDCl3) δ 1.00-1.38 (m, 6H); 3.20-3.38 (m, 2H); 3.50-3.70 (m, 2H); 3.86 (s, 3H); 7.10-7.40 (m, 4H); 7.48 (d, 2H, J=8.4 Hz); 7.84 (d, 2H, J=8.4 Hz). Anal. calc. for C19H21NO3: C, 73.29; H, 6.80; N, 4.50. Found: C, 73.11; H, 6.78; N, 4.49.

Workup

  1. stirringThe obtained mixture is stirred at room temperature for 14 hours
  2. washwashed in a first step with saturated aqueous sodium bicarbonate and in a second step with water
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue that is recovered
  6. customis purified by flash chromatography (ligroin/ethyl acetate 1/1 v/v)

Sources & evidence

ORD record
ord-335805112ae14059a278ddcc348dfe1a
Source dataset
uspto-grants-2013_12
Patent number
US08609659B2

Reaction notes

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