Acetic Anhydride → 1-Acetyl-1,2-bis(methylsulfonyl)-2-(2-chloroethyl)hydrazine
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](OC(=O)C)(=[O:16])[CH3:15].C(N(CC)CC)C>CC(C)=O>[C:14]([N:6]([S:7]([CH3:10])(=[O:9])=[O:8])[N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:11][CH2:12][Cl:13])(=[O:16])[CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)hydrazine (1.5 g, 0.006 mol) and acetic anhydride (4.3 g, 0.042 mol) in dry acetone (50 mL), triethylamine (3.6 g, 0.035 mol) was added dropwise at room temperature. After an additional 16 h, the reaction mixture was evaporated to dryness. The residue was taken up in ethyl acetate (50 mL) and washed with dilute hydrochloric acid (3×10 mL), followed by water (3×10 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate, treated with charcoal and filtered. On evaporation of the solvent a solid was obtained which, on recrystallization from ethanol, gave 1.1 g (62.8%) of the title compound: mp 148°-149° C.; 1H NMR (acetone-d6) δ 3.8-4.2 (m, 4 H, CH2CH2), 3.5 and 3.3 (2 s, 6 H, 2CH3SO 2), 2.4 (s, 3 H, CH3CO). Anal. (C6H13C1N2O5S2) C, H, N.
Workup
- customthe reaction mixture was evaporated to dryness
- washwashed with dilute hydrochloric acid (3×10 mL)
- dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
- additiontreated with charcoal
- filtrationfiltered
- customOn evaporation of the solvent a solid
- customwas obtained which
- customon recrystallization from ethanol
Sources & evidence
- ORD record
- ord-103f8d386bb24d57bd3b91c0d79748e9
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05256820
Reaction notes
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