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

HRID 2101234Notes

Reaction equation

HRID 2101234 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-1461712e0ec54459bfbb1f31b3dfc44c
Source dataset
uspto-grants-2009_08
Patent number
US07572825B2

Reaction notes

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