3-Methoxy-4-(phenylmethoxy)benzoyl chloride → N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-3-methoxy-4-benzyloxybenzamide

HRID 967864Notes

Reaction equation

HRID 967864 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](Cl)=[O:7].[NH2:20][C:21]1[CH:22]=[C:23]([NH:28][C:29](=[O:39])[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([N:36]([CH3:38])[CH3:37])[CH:31]=2)[CH:24]=[CH:25][C:26]=1[CH3:27]>C(Cl)Cl>[CH3:38][N:36]([CH3:37])[C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[C:29]([NH:28][C:23]1[CH:24]=[CH:25][C:26]([CH3:27])=[C:21]([NH:20][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:22]=1)=[O:39]

Participants

4

Reactant 2

HCID 111193663-Methoxy-4-(phenylmethoxy)benzoyl chlorideHCID 22057981HCID 22057981, compound

Product 1

HCID 22291053N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-3-methoxy-4-benzyloxybenzamideYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methoxy-4-benzyloxybenzoyl chloride (3.01 g) in methylene chloride (50 ml) was added to a stirred suspension of N-(3-amino-4-methylphenyl)-3-dimethylaminobenzamide (2.69 g) in methylene chloride (30 ml) and the reaction mixture was stirred at ambient temperature for 16 hours. The organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution, dried and evaporated. The solid residue was stirred in diethyl ether for 16 hours, filtered and dried to give N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-3-methoxy-4-benzyloxybenzamide (0.458 g); NMR: (DMSOd6) 2.18 (s, 3H), 2.96 (s, 6H), 3.82 (s, 3H), 5.12 (s, 2H), 6.9 (m, 1H), 7.16 (t, 1H), 7.21 (d, 2H), 7.3 (t, 2H), 7.4 (m, 5H), 7.57 (m, 3H), 7.78 (d, 1H), 9.75 (s, 1H), 10.18 (s, 1H).

Workup

  1. washThe organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution
  2. customdried
  3. customevaporated
  4. stirringThe solid residue was stirred in diethyl ether for 16 hours
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-a2760aefdb38497d8a1c6d881ac1bff5
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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