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Propofol → Dodecyl[[2,6-Bis(1-methylethyl)phenoxy]sulfonyl]carbamate

HRID 5642
Notes
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Reaction equation

HRID 5642 reaction equation
[CH2:1]([O:13][C:14](=[O:20])[NH:15][S:16](Cl)(=[O:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[OH:33])([CH3:23])[CH3:22].C(N(CC)CC)C>C1COCC1>[CH3:31][CH:30]([C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH:21]([CH3:23])[CH3:22])[C:25]=1[O:33][S:16]([NH:15][C:14](=[O:20])[O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:17])=[O:18])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4943PropofolHCID 8471TriethylamineHCID 10758631Dodecyl(chlorosulfonyl)carbamate

Product 1

HCID 10648021Dodecyl[[2,6-Bis(1-methylethyl)phenoxy]sulfonyl]carbamateYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-dodecyl(chlorosulfonyl)carbamate (5.0 g, 15.2 mmoles) in 80 mL THF was added dropwise to a solution of 2,6-diisopropyl phenol (2.72 g, 15.2 mmoles) and excess triethylamine in 100 mL THF at room temperature under an atmosphere of N2. The mixture was stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between 1N HCl and EtOAc. The organic layer was dried with MgSO4, filtered, and evaporated to give a clear oil. Chromatography (SiO2, 5% EtOAc/hexanes) gave 4.26 g of the title compound as a waxy solid, mp 32°-35° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 1N HCl and EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a clear oil

Sources & evidence

ORD record
ord-29c831e9f5614f9b8eb8037523a00d0e
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05245068

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes