Triethylamine → N-Methoxy-N-methyl-4-phenylbenzamide

HRID 1817673Notes

Reaction equation

HRID 1817673 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.Cl.[CH3:17][NH:18][O:19][CH3:20].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:20][O:19][N:18]([CH3:17])[C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:2][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 841514-Phenylbenzoyl chloride

Product 1

HCID 10060247N-Methoxy-N-methyl-4-phenylbenzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4-Biphenylcarbonyl chloride (8 g) was suspended in chloroform (30 mL). This was added dropwise to a stirred solution of N,O-dimethyl hydroxylamine hydrochloride (5.2 g) and triethylamine (13.5 mL) in chloroform (80 mL) at 0° C. After addition was complete, the mixture was allowed to warm to room temperature and was stirred for a further 30 minutes. The organic phase was separated, washed with water and dried over MgSO4. Evaporation gave an oil, purified by flash column chromatography (ethyl acetate: light petroleum, 1:1) to give the title compound as a white solid. δC (CDCl3, 62.9 MHz): 33.8, 61.1, 126.7, 127.2, 127.9, 128.9, 132.8, 140.2, 143.4 and 169.7. δH (CDCl3, 250 MHz): 3.38 (3H, s), 3.59 (3H, s), 7.37-7.48 (3H, m), 7.61 (4H, m) and 7.77 (2H, d, J 8.5).

Workup

  1. additionAfter addition
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customEvaporation
  6. customgave an oil
  7. custompurified by flash column chromatography (ethyl acetate: light petroleum, 1:1)

Sources & evidence

ORD record
ord-1c30f39a80ae4cf4beb4852ed08d53cb
Source dataset
uspto-grants-2009_10
Patent number
US07598289B2

Reaction notes

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