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

HRID 1269620Notes

Reaction equation

HRID 1269620 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[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:23]([C:26]1[CH:38]=[CH:37][C:29]([O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:28]([CH3:39])[CH:27]=1)(=[O:25])=[O:24].C(N(CC)CC)C.S(Cl)(Cl)(=O)=O>C(Cl)Cl.O>[CH2:1]([N:5]([C:6]1[CH:7]=[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:23]([C:26]1[CH:38]=[CH:37][C:29]([O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:28]([CH3:39])[CH:27]=1)(=[O:25])=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 24648Sulfuryl chlorideHCID 11415129Ethyl 4-chlorosulfonyl-2-methylphenoxyacetateHCID 18448424N-Butyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amine

Product 1

HCID 58622863Ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetateYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-butyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (0.128 g, 0.44 mmol) In anhydrous CH2Cl2 (10 mL) was added ethyl [4-(chlorosulfonyl)-2-methylphenoxy]acetate (0.121 g, 0.41 mmol) and triethylamine (0.122 mL, 0.87 mmol). The resultant mixture was stirred for 24 h at room temperature prior to addition of sulfonyl chloride (0.121 mg, 0.41 mmol) and triethylamine (0.122 mL, 0.87 mmol). After a further 18 h stirring at room temperature the reaction was diluted with water (10 mL) and extracted with CH2Cl2 (2×10 mL). The organic solution was dried (Na2SO4) and the solvents removed in vacuo. Purification by SPE (Silica, 10 g) eluting 49:1–19:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (0.182 g).

Workup

  1. extractionextracted with CH2Cl2 (2×10 mL)
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. customthe solvents removed in vacuo
  4. customPurification by SPE (Silica, 10 g)
  5. washeluting 49:1–19:1 cyclohexane

Sources & evidence

ORD record
ord-8a78a4cff166489eb3f838fd61bb35d4
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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