Triethylamine → 38202-27-6

HRID 717853Notes

Reaction equation

HRID 717853 reaction equation
[OH:1]/[N:2]=[C:3](/[O:5][CH2:6][CH3:7])\[CH3:4].C(N(CC)CC)C.[C:15]1([CH3:27])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[S:23](Cl)(=[O:25])=[O:24]>CN(C)C=O.C(Cl)Cl>[C:15]1([CH3:27])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[S:23]([O:1]/[N:2]=[C:3](/[O:5][CH2:6][CH3:7])\[CH3:4])(=[O:24])=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 5363167Ethyl N-hydroxyacetimidate

Product 1

HCID 628244438202-27-6Yield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The ethyl (1E)-N-hydroxyethanimidoate (4.72 g, 45.7 mmol) was dissolved in N,N-dimethylformamide (12.0 mL) and triethylamine (6.37 mL, 45.7 mmol) and cooled in an ice bath. The mesitylenesulfonyl chloride (10.0 g, 45.7 mmol) was added portion wise over 5 minutes and the reaction was stirred vigorously for 30 minutes. The reaction mixture became a thick syrup. The reaction was diluted with methylene chloride (100 mL) and was washed with water 3×, brine, dried over magnesium sulfate and concentrated to give ethyl (1E)-N-[(mesitylsulfonyl)oxy]ethanimidoate (11.2 g, 86%) as a semi-solid residue. LCMS calculated for C13H20NO4S (M+H)+: m/z=286.1. found: 285.9.

Workup

  1. washwas washed with water 3×, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2820ac3431a5451e88bc571ca9ead4da
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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