Triethylamine → HCID 22006820, compound

HRID 323660Notes

Reaction equation

HRID 323660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])[CH:5]=[C:6]([Cl:12])[C:7]=1[O:8][CH2:9][CH2:10][NH2:11].C(N(CC)CC)C.[F:26][C:27]([F:40])([F:39])[O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])[CH:5]=[C:6]([Cl:12])[C:7]=1[O:8][CH2:9][CH2:10][NH:11][S:35]([C:32]1[CH:31]=[CH:30][C:29]([O:28][C:27]([F:26])([F:39])[F:40])=[CH:34][CH:33]=1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 220067523,5-Dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

Product 1

HCID 22006820HCID 22006820, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.20 g of 3,5-dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene and 0.10 g of triethylamine dissolved in 5 ml of dichloromethane was added dropwise a solution of 0.16 g of 4-trifluoromethoxybenzenesulfonyl chloride dissolved in 5 ml of dichloromethane, while stirring under ice cooling. After stirring at room temperature for 6 hours, the reaction mixture was concentrated to give a residue. The residue was subjected to silica gel chromatography, which afforded 0.20 g of 3,5-dichloro-4-(2-(4-trifluoromethoxybenzenesulfonamido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene (60% yield), nD23.0 1.5470.

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. concentrationthe reaction mixture was concentrated
  3. customto give a residue

Sources & evidence

ORD record
ord-d825d40c189142eaa0a228cf537d226a
Source dataset
uspto-grants-2001_04
Patent number
US06214835B1

Reaction notes

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