tert-Butanol → HCID 18379696, compound

HRID 2299067Notes

Reaction equation

HRID 2299067 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8].[NH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([NH:13][S:7](=[O:9])(=[O:8])[NH:10][C:11]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:12])[CH:15]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 100093-AminopyridineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 18379696HCID 18379696, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butanol (2.0 mL, 21.1 mmol) was added to a solution of chlorosulfonyl- isocyanate (1.8 mL, 21.1 mmol) in CH2Cl2 (40 mL). The reaction mixture was stirred at ambient temperature for 0.5 hours and then treated with a solution of 3-aminopyridine (2.00 g, 21.1 mmol) and triethylamine (4.4 mL, 31.6 mmol) in CH2Cl2 (20 mL) via canula. The reaction mixture was stirred at ambient temperature for an additional 1.5 hours and then filtered through a 0.25 inch silica gel plug. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel (elution with EtOAc) to provide 1.17 g of the title compound as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for an additional 1.5 hours
  2. filtrationfiltered through a 0.25 inch silica gel plug
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (elution with EtOAc)

Sources & evidence

ORD record
ord-d9fab641ea9d46569df65c0bb5cfdb67
Source dataset
uspto-grants-2002_12
Patent number
US06495576B2

Reaction notes

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