1,2-Bis(tert-butylsulfonyl)acetylene → HCID 15232946, compound

HRID 1769026Notes

Reaction equation

HRID 1769026 reaction equation
[C:1]([S:5]([C:8]#[C:9][S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[N:17]([CH2:20][N:21]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][C:27]([O:36][CH3:37])=[CH:28][C:29]=2[CH:33]([CH3:35])[CH3:34])[S:22]1(=[O:24])=[O:23])=[N+:18]=[N-:19]>C1C=CC=CC=1>[C:1]([S:5]([C:8]1[N:19]=[N:18][N:17]([CH2:20][N:21]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][C:27]([O:36][CH3:37])=[CH:28][C:29]=3[CH:33]([CH3:35])[CH3:34])[S:22]2(=[O:23])=[O:24])[C:9]=1[S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])(=[O:6])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 129742521,2-Bis(tert-butylsulfonyl)acetyleneHCID 152910912-Azidomethyl-4-isopropyl-6-methoxysaccharin

Product 1

HCID 15232946HCID 15232946, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Di(t-butylsulfonyl)acetylene (1.50 g.) was added to part (75 mL) of the above-described solution of 2-azidomethyl-4-isopropyl-6-methoxysaccharin in benzene. The resulting solution was heated under reflux for 65 hours, then chromatographed on silica gel (Kieselgel 60, 68 g) using first benzene and then cyclohexane-ethyl acetate (90:10, then 85:15, then 75:25) as eluant. The fractions containing the product, which were identified by thin layer chromatography, were combined and recrystallized from benzene-cyclohexane. Pan (0.5 g) of the resulting product (1.5 g, m.r. 204°-205° C., 26% yield for both steps) was recrystallized twice from ethyl acetate affording 2-[4,5-di(t-butylsulfonyl)-1,2,3-triazol-1-yl]methyl-4-isopropyl-6-methoxysaccharin as pale yellow elongated prisms (0.15 g, m.r. 207.5°-209° C.).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 65 hours
  3. customchromatographed on silica gel (Kieselgel 60, 68 g)
  4. additionThe fractions containing the product, which
  5. customrecrystallized from benzene-cyclohexane
  6. custom204°-205° C., 26% yield for both steps) was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-f59535f1d38f41d2ba39258c71ce6d1a
Source dataset
uspto-grants-1995_01
Patent number
US05380737

Reaction notes

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