Triethylamine → Ethyl [4-({butyl[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate

HRID 1269669Notes

Reaction equation

HRID 1269669 reaction equation
[CH2:1]([NH:5][C:6]1[C:7]([CH3:22])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].Cl[S:24]([C:27]1[CH:39]=[CH:38][C:30]([O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:29]([CH3:40])[CH:28]=1)(=[O:26])=[O:25].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:5]([C:6]1[C:7]([CH3:22])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)[S:24]([C:27]1[CH:39]=[CH:38][C:30]([O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:29]([CH3:40])[CH:28]=1)(=[O:26])=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11415129Ethyl 4-chlorosulfonyl-2-methylphenoxyacetateHCID 18448423N-Butyl-N-[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amine

Product 1

HCID 58622885Ethyl [4-({butyl[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetateYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-butyl-N-[2-methyl-4′-(trifluoromethyl)-1,1′-biphenyl-3-yl)amine (58 mg, 0.19 mmol) in anhydrous CH2Cl2 (5 mL) was added ethyl [4-(chlorosulfonyl)-2-methylphenoxy]acetate (83 mg, 0.28 mmol) and triethylamine (0.052 mL, 0.38 mmol). The resulting solution was stirred 20 h at room temperature under nitrogen. The reaction was diluted with CH2Cl2 (50 mL), and the organic solution washed with aq. sat. NaHCO3 (10 mL) and brine (10 mL). The organic extract was separated by hydrophobic frit and evaporated. Purification by mass directed autoprep afforded the title compound as a colourless oil (15 mg).

Workup

  1. washthe organic solution washed with aq. sat. NaHCO3 (10 mL) and brine (10 mL)
  2. extractionThe organic extract
  3. customwas separated by hydrophobic frit
  4. customevaporated
  5. customPurification by mass

Sources & evidence

ORD record
ord-4cba500b50b6454dbce16ccabdbdd0a4
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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