Triethylamine → 38202-27-6

HRID 2272823Notes

Reaction equation

HRID 2272823 reaction equation
[OH:1]/[N:2]=[C:3](/[O:5][CH2:6][CH3:7])\[CH3:4].C(N(CC)CC)C.[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24](Cl)(=[O:26])=[O:25]>CN(C=O)C>[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24]([O:1]/[N:2]=[C:3](/[O:5][CH2:6][CH3:7])\[CH3:4])(=[O:25])=[O:26]

Participants

5

Reactant 3

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

Product 1

HCID 628244438202-27-6Yield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl (1E)-N-hydroxyethanimidate (8.4 g, 81.5 mmol) in DMF (20 mL) is added triethylamine (12 mL, 86.24 mmol) and the mixture is stirred for 20 minutes. 2,4,6-Trimethylbenzene-1-sulfonyl chloride (20 g, 81.5 mmol) is added and the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is quenched with water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts are dried over sodium sulphate, filtered, and evaporated to dryness to give the title compound as white solid (15 g, 64%). The crude material is used without further purification.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 16 hours
  2. customThe reaction mixture is quenched with water (100 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ac5865e2dcdc4a608ac1c14297bbddea
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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