Dimethylformamide → HCID 58980909, compound

HRID 1181802Notes

Reaction equation

HRID 1181802 reaction equation
[Si:1]([NH:8][S:9]([C:12]1[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=1)(=[O:11])=[O:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN1C=C(S(N)(=O)=O)N=C1.[Si](Cl)(C(C)(C)C)(C)C.C(N(CC)CC)C.CN([CH:46]=[O:47])C>>[Si:1]([NH:8][S:9]([C:12]1[N:13]=[C:14]([CH:46]=[O:47])[N:15]([CH3:17])[CH:16]=1)(=[O:10])=[O:11])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 27368851-methyl-1H-imidazole-4-sulfonamideHCID 69429123HCID 69429123, compound

Product 1

HCID 58980909HCID 58980909, compound

Procedure

Step A) Preparation of N-[tert-butyl(dimethyl)silyl]-1-methyl-1H-imidazole-4-sulfonamide: A mixture of 2.2 g (14 mmol) 1-methyl-1H-imidazole-4-sulfonamide, 2.1 g (14 mmol) t-butyldimethylsilyl chloride and 3.9 mL (28 mmol) triethylamine in 15 mL DMF was stirred at room temperature overnight Solvent was removed, and the residue was dissolved in EtOAc before being washed with water and brine. Drying (MgSO4) and removal of solvent gave 3 g of the subtitle product as a white solid, 1H NMR (DMSO) δ 7.7 (s, 1H), 7.6 (s, 1H), 7.35 (s, 1H), 3.7 (s, 3H), 0.9 (s, 9H)., 0.2 (s, 6H).

Workup

  1. customwas removed
  2. dissolutionthe residue was dissolved in EtOAc
  3. washbefore being washed with water and brine
  4. customDrying
  5. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-721bac0bd11448f98c29465f9abf2cb4
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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