Triethylamine → HCID 58696299, compound

HRID 1178328Notes

Reaction equation

HRID 1178328 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([C:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)([CH2:13][OH:14])[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.N1C=CC=CC=1.S(=O)(=O)=O>CS(C)=O>[C:1]([O:5][C:6](=[O:23])[N:7]([C:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)([CH:13]=[O:14])[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 58696361HCID 58696361, compound

Product 1

HCID 58696299HCID 58696299, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

tert-Butyl[1-(3,4-dichlorophenyl)-1-hydroxymethyl-3-butenyl]methylcarbamate (45 g) was dissolved in anhydrous dimethyl sulfoxide (320 mL), and triethylamine (87 mL) was added thereto. Under cooling with ice, sulfur trioxide-pyridine (31.7 g) was added, and the resultant mixture was stirred for 1 hour at room temperature. Ice-water (650 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (500 mL). The organic layer was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby give the title compound (35.5 g, 77%).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate (500 mL)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-5d1997c05fc44f6b8bd2722cda3cba30
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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