Triethylamine → HCID 9816856, compound

HRID 1275676Notes

Reaction equation

HRID 1275676 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11](Cl)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][NH:16][CH2:17][C:18]#[CH:19].C(N(CC)CC)C>O1CCCC1>[CH2:17]([N:16]([CH3:15])[S:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:13])=[O:12])[C:18]#[CH:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96160N-methylpropyn-2-ylamineHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 9816856HCID 9816856, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dimethoxybenzene sulfonyl chloride (11.8 g) in tetrahydrofuran (100 mL) is added slowly with stirring to a mixture of N-methylpropargylamine (3.5 g), triethylamine (5.05 g), and tetrahydrofuran (100 mL). The resulting mixture is refluxed 1 hour, cooled, filtered, and evaporated to dryness. The residue is treated with water, filtered, washed with water, and dried. Recrystallization from ethanol gave 8.7 g of the title product.

Workup

  1. temperatureThe resulting mixture is refluxed 1 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated to dryness
  5. additionThe residue is treated with water
  6. filtrationfiltered
  7. washwashed with water
  8. customdried
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-100e0508de944cc9ae2225a1247a772a
Source dataset
uspto-grants-2000_12
Patent number
US06162830

Reaction notes

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