Triethylamine → HCID 59202377, compound

HRID 1967648Notes

Reaction equation

HRID 1967648 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:3]=1[NH2:4].[CH3:20][O:21][C:22]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[C:27]([O:34][CH3:35])[C:23]=1[C:24](O)=[O:25].C(N(CC)CC)C.O=C1N([ClH]P([ClH]N2CCOC2=O)=O)CCO1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>ClCCl>[CH3:19][C:5]1[CH:6]=[C:7]([C:9]([F:18])([C:10]([F:12])([F:13])[F:11])[C:14]([F:15])([F:16])[F:17])[CH:8]=[C:2]([CH3:1])[C:3]=1[NH:4][C:24](=[O:25])[C:23]1[C:27]([O:34][CH3:35])=[CH:28][CH:29]=[C:30]([N+:31]([O-:33])=[O:32])[C:22]=1[O:21][CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 30850942,6-Dimethoxy-3-nitrobenzoic acidHCID 98824254-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2,6-dimethylaniline

Product 1

HCID 59202377HCID 59202377, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-aniline (145 mg, 0.5 mmol) and 2,6-dimethoxy-3-nitrobenzoic acid (136 mg, 0.6 mmol) in dichloromethane (10 ml) was added triethylamine (210 μl, 1.5 mmol) and bis(2-oxo-3-oxazolidinyl)phosphonic chloride “BOP-Cl” (153 mg, 0.6 mmol). The reaction mixture was heated to reflux for 48 hours. The reaction mixture was cooled to ambient temperature and quenched by the addition of a saturated sodium bicarbonate solution (10 ml). The phases were separated, the organic phase was dried over sodium sulfate and concentrated. Purification by chromatography over silica gel (eluent: hexane/ethyl acetate 2:1) gave N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,6-dimethoxy-3-nitrobenzamide (222 mg, 89% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 48 hours
  3. customquenched by the addition of a saturated sodium bicarbonate solution (10 ml)
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by chromatography over silica gel (eluent: hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-c36746374c3f409f8d183b5ddb6017da
Source dataset
uspto-grants-2013_04
Patent number
US08420855B2

Reaction notes

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