Triethylamine → HCID 15652326, compound

HRID 1657232Notes

Reaction equation

HRID 1657232 reaction equation
[CH3:1][S:2]([N:5]([CH2:11][CH2:12][Cl:13])[NH:6][S:7]([CH3:10])(=[O:9])=[O:8])(=[O:4])=[O:3].[C:14](Cl)(=[O:17])[CH2:15][CH3:16].C(N(CC)CC)C>CC(C)=O>[CH3:1][S:2]([N:5]([CH2:11][CH2:12][Cl:13])[N:6]([S:7]([CH3:10])(=[O:9])=[O:8])[C:14](=[O:17])[CH2:15][CH3:16])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 10198873VPN-4090CE

Product 1

HCID 15652326HCID 15652326, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)hydrazine (1.25 g, 0.005 mol) and propionyl chloride (3.20 g, 0.035 mol) in dry acetone (20 mL), triethylamine (0.014 mol) was added dropwise at room temperature. A precipitate was formed immediately. After an additional 20 h, the reaction mixture was filtered and the filtrate evaporated in dryness in vacuo. The residue was taken up in ethyl acetate (100 mL) and washed with dilute hydrochloric acid (3×15 mL), followed by water (2×10 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated to dryness in vacuo. The residue was triturated with petroleum ether to give a solid which, on recrystallization from absolute ethanol, afforded 0.71 g (46.4%) of the title compound: mp 97°-98° C.; 1H NMR (acetone-d6) δ 3.8-4.2 (m, 4 H, CH2CH2), 3.5 and 3.3 (2 s, 6 H, 2 CH3SO2), 2.8 (q, 2 H, COCH2), 1.1 (t, 3 H, COCCH3). Anal. (C7H15C1N2O5S2) C, H, N.

Workup

  1. customA precipitate was formed immediately
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate evaporated in dryness in vacuo
  4. washwashed with dilute hydrochloric acid (3×15 mL)
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated to dryness in vacuo
  8. customThe residue was triturated with petroleum ether
  9. customto give a solid which
  10. customon recrystallization from absolute ethanol

Sources & evidence

ORD record
ord-05db39ba922d4a0f92df28a627f7b053
Source dataset
uspto-grants-1993_10
Patent number
US05256820

Reaction notes

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