Triethylamine → HCID 10689322, compound

HRID 1637384Notes

Reaction equation

HRID 1637384 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][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[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][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:21])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82128Carbonochloridic acid, 4-methoxyphenyl esterHCID 1306301,2-Bis(methylsulfonyl)-1-methylhydrazine

Product 1

HCID 10689322HCID 10689322, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,2-Bis(methylsulfonyl)-2-[(4-methoxyphenoxy)carbonyl]-1-methylhydrazine (compound 9) was synthesized as follows: Triethylamine (0.269 g, 0.0029 mol) was added to a stirred solution of 1,2-bis(methylsulfonyl)-1-methylhydrazine (0.50 g, 0.0025 mol) and 4-methoxyphenyl chloroformate (0.63 g, 0.0033 mol) in acetone (30 ml) and the mixture stirred for 1 hr. The reaction mixture was filtered and the filtrate evaporated to dryness in vacuo. The residue was triturated with petroleum ether (5 ml) and the petroleum ether layer decanted. Column chromatography of the residue on silica gel (70-270 mesh, 60 Angstroms, CHCl3), followed by crystallization from ethanol gave 0.14 g (16.1%) of the desired compound. Mp was approximately 101-102° C. 1H NMR (acetone-d6) : δ 7.3 and 7.0 (4H, 2d, aromatic H), 3.9 (3H, s, OCH3), 3.6, 3.4 and 3.2 (9H, 3s, 2 CH3SO2 and NCH3).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated to dryness in vacuo
  3. customThe residue was triturated with petroleum ether (5 ml)
  4. customthe petroleum ether layer decanted
  5. customColumn chromatography of the residue on silica gel (70-270 mesh, 60 Angstroms, CHCl3), followed by crystallization from ethanol

Sources & evidence

ORD record
ord-dcadcecf7af045f18559055427093f27
Source dataset
uspto-grants-2000_03
Patent number
US06040338

Reaction notes

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