(Diethylamino)sulfur trifluoride → HCID 10520508, compound

HRID 2084712Notes

Reaction equation

HRID 2084712 reaction equation
O[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:4]=1.C(N(S(F)(F)[F:30])CC)C>ClCCl>[F:30][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:4]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10471772HCID 10471772, compound

Product 1

HCID 10520508HCID 10520508, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the alcohol from Step 3 (212 mg, 0.64 mmol) in dichloromethane (4 mL) was added diethylaminosulfur trifluoride (0.13 mL, 1.0 mmol). The reaction mixture was stirred at room temperature for 3 hours and partitioned between water and dichloromethane. The aqueous solution was extracted with dichloromethane. The organic solution was washed with brine and concentrated. The residue was chromatographed on silica (1:1 hexane:ethyl acetate) to give the desired product (72 mg, 34%): mp 162-163° C.; Anal. calc'd for C16H14N3O2SF: C, 58.00; H, 4.26; N, 12.68. Found: C, 57.95; H, 4.03; N, 12.58.

Workup

  1. custompartitioned between water and dichloromethane
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. washThe organic solution was washed with brine
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica (1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-d33ba178664b4cb499244b3701791dd1
Source dataset
uspto-grants-2004_04
Patent number
US06716991B1

Reaction notes

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