Triethylamine → HCID 10760500, compound

HRID 1637383Notes

Reaction equation

HRID 1637383 reaction equation
C(N(CC)CC)C.[CH3:8][S:9]([N:12]([CH3:18])[NH:13][S:14]([CH3:17])(=[O:16])=[O:15])(=[O:11])=[O:10].Cl[C:20]([O:22][CH2:23][CH2:24][Br:25])=[O:21]>CC(C)=O>[CH3:8][S:9]([N:12]([CH3:18])[N:13]([S:14]([CH3:17])(=[O:15])=[O:16])[C:20]([O:22][CH2:23][CH2:24][Br:25])=[O:21])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 785282-Bromoethyl chloroformateHCID 1306301,2-Bis(methylsulfonyl)-1-methylhydrazine

Product 1

HCID 10760500HCID 10760500, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,2-Bis(methylsulfonyl)-2-(2-bromoethoxycarbonyl)-1-methylhydrazine (compound 8) was synthesized as follows: Triethylamine (1.45 g, 0.014 mol) was added in portions to a stirred solution of 1,2-bis(methylsulfonyl)-1-methylhydrazine (2.02 g, 0.01 mol) and 2-bromoethyl chloroformate (3.49 g, 0.019 mol) in acetone (100 ml) over a period of 15 min. The reaction mixture was stirred for an additional 18 hr, filtered, and the filtrate evaporated to dryness in vacuo. The residue was taken up in chloroform (100 ml) and washed with water (3×20 ml). The chloroform layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated to dryness. The residue was triturated with petroleum ether until a solid separated. The solid was filtered and recrystallized from ethanol (1.52 g, 43.0%). Mp was approximately 81-82° C. 1H NMR (CDCl3): δ 4.7 and 3.6 (4H, 2t, CH2CH2Br), 3.5, 3.3 and 3.1 (9H, 3s, 2CH3SO2 and NCH3).

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness in vacuo
  3. washwashed with water (3×20 ml)
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated to dryness
  7. customThe residue was triturated with petroleum ether until a solid
  8. customseparated
  9. filtrationThe solid was filtered
  10. customrecrystallized from ethanol (1.52 g, 43.0%)

Sources & evidence

ORD record
ord-ca28403d03ad4a80b3c5eb01499c9e98
Source dataset
uspto-grants-2000_03
Patent number
US06040338

Reaction notes

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