(Diethylamino)sulfur trifluoride → HCID 10520508, compound

HRID 962840Notes

Reaction equation

HRID 962840 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, compound

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 organic solution was washed with brine and concentrated. The residue was chromatographed on silica (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. washThe organic solution was washed with brine
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica (72 mg, 34%)

Sources & evidence

ORD record
ord-fa490df99d8f4b7bbae3fe01123b4b74
Source dataset
uspto-grants-1998_06
Patent number
US05760068

Reaction notes

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