Water → 2',4'-Dichloro-biphenyl-4-carboxylic acid methoxy-methyl-amide

HRID 227890Notes

Reaction equation

HRID 227890 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](Cl)=[O:16])=[CH:11][CH:10]=1.[CH3:18][NH:19][O:20][CH3:21].C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[CH3:21][O:20][N:19]([CH3:18])[C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:10][CH:11]=1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 577572502',4'-Dichloro-biphenyl-4-carbonyl chloride

Product 1

HCID 577572372',4'-Dichloro-biphenyl-4-carboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2′,4′-Dichloro-biphenyl-4-carbonyl chloride was dissolved in chloroform (10 mL) and added dropwise to a chilled solution of N,O-dimethyl hydroxylamine (2.5 g) and triethylamine (7 mL) in chloroform (40 mL). Following addition, the mixture was allowed to warm to room temperature and stirred for a further 30 minutes. The mixture was poured into water and the organic phase separated, washed with water, and dried. Evaporation gave an oil, which was purified by column chromatography (petrol/ethyl acetate) to give a pale yellow oil which slowly crystallised upon standing to give the title compound as a white solid. 13C NMR (CDCl3): δ 33.8, 61.2, 127.3, 128.2, 129.1, 129.9, 132.0, 133.2, 133.5, 134.2, 138.3, 140.5 and 169.5. 1H NMR (CDCl3): δ 3.39 (3H, s), 3.58 (3H, s), 7.26 (2H, m), 7.45 (2H, d, J=8.5 Hz), 7.54 (1H, s) and 8.08 (2H, d, J=8.5 Hz).

Workup

  1. additionaddition
  2. customthe organic phase separated
  3. washwashed with water
  4. customdried
  5. customEvaporation
  6. customgave an oil, which
  7. customwas purified by column chromatography (petrol/ethyl acetate)
  8. customto give a pale yellow oil which
  9. customslowly crystallised

Sources & evidence

ORD record
ord-8c92664541dd458bbfc23d1637359098
Source dataset
uspto-grants-2009_07
Patent number
US07560597B2

Reaction notes

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