Methanesulfonyl chloride → HCID 178425305, compound

HRID 1197285Notes

Reaction equation

HRID 1197285 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CS(Cl)(=O)=O.[C:14]([N:18]([C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1)[NH2:19])([CH3:17])([CH3:16])[CH3:15].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CC(C)=O.C(N(CC)CC)C>[C:14]([N:18]([C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1)[NH:19][C:6]([C:4]1[N:3]=[N:2][NH:1][CH:5]=1)=[O:8])([CH3:17])([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 1401204-Carboxy-1,2,3-triazoleHCID 516892Sodium BicarbonateHCID 15452040N'-t-butyl-N'-(3-methylbenzoyl)hydrazine

Product 1

HCID 178425305HCID 178425305, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1,2,3-triazole-4-carboxylic acid (1.0 g) and triethylamine (0.9 g) were dissolved in 40 ml methylene chloride and cooled in an ice bath. Methanesulfonylchloride (1.0 g) was added dropwise. After addition was complete, the reaction mixture was stirred for 0.5 hours. N'-t-butyl-N'-(3methylbenzoyl)hydrazine (1.84 g) in 10 ml CH2Cl2 was added dropwise. The resulting mixture was allowed to stand for 14 hours. Aqueous sodium bicarbonate was added. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give a yellow oil. Chromatography on silica gel using acetone as eluant afforded N'-t-butyl-N-1,2,3-triazole-4-carbonyl-N'-(3-methylbenzoyl)hydrazine.

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter addition
  3. waitto stand for 14 hours
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-4b5452a71bb34975b28024658766224a
Source dataset
uspto-grants-1992_05
Patent number
US05117057

Reaction notes

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