Triethylamine → 1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

HRID 717547Notes

Reaction equation

HRID 717547 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].[OH:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>C(OC)(C)(C)C>[C:18]([O:17][C:16](=[O:22])[NH:15][O:14][S:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])(=[O:12])=[O:11])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

2,4,6-trimethylbenzenesulfonyl chloride (5 g, 0.022 mol) was added to a solution of methyl tertiary-butyl ether (50 mL) under nitrogen atmosphere at 0° C., followed by the addition of tert-butyl hydroxycarbamate (3.04 g, 0.22 mol) at 0° C. Next, triethylamine (3.24 mL, 0.023 mol) was added drop wise to the reaction mixture, which was then it was allowed to stir for 2 h. The reaction product was filtered through sintered funnel and the filtrate was concentrated under vacuum up to ¾ volume. Hexane (50 mL) was added to the concentrated filtrate, which was then stirred for 20 min wherein a precipitate formed. The participate was collected by filtration and the solid dried to afford tert-butyl(mesitylsulfonyl)oxycarbamate. 1H NMR (400 MHz, CDCl3) δ 8.49 (s, 1H), 8.31 (s, 1H), 2.38 (s, 9H). MS (M+1): 316.3.

Workup

  1. filtrationThe reaction product was filtered through sintered funnel
  2. concentrationthe filtrate was concentrated under vacuum up
  3. additionHexane (50 mL) was added to the concentrated filtrate, which
  4. stirringwas then stirred for 20 min wherein a precipitate
  5. customformed
  6. filtrationThe participate was collected by filtration
  7. customthe solid dried

Sources & evidence

ORD record
ord-2e24fd8b03254630a0f1fcac84bfd542
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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