(Diethylamino)sulfur trifluoride → HCID 90204253, compound

HRID 1480195Notes

Reaction equation

HRID 1480195 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]1(O)[CH2:14][CH2:13][CH2:12]1.CCN(S(F)(F)[F:24])CC>ClCCl>[F:24][C:11]1([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C:2]([F:17])([F:16])[F:1])[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 90204115HCID 90204115, compound

Product 1

HCID 90204253HCID 90204253, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[4-(2,2,2-Trifluoro-ethoxy)-pyridin-3-yl]-cyclobutanol (example 108b, 1.7 g, 6.88 mmol) in dry dichloromethane (25.0 ml) under an argon atmosphere cooled down to 0° C. was added DAST (1.36 ml, 10.3 mmol). The reaction mixture was stirred at 0° C. for 30 minutes. The reaction was quenched by addition of a 2M aqueous solution of sodium carbonate and the bi-phasic mixture was stirred for 20 minutes. The bi-phasic mixture was transferred into a separatory funnel and the organic phase was collected. The organic phase was dried over sodium sulfate and evaporated down to dryness to yield the title compound (1.68 g, 98%); MS (ESI, m/z): 250.4 (M+H+). The crude material was used without any purification for the next step.

Workup

  1. customThe reaction was quenched by addition of a 2M aqueous solution of sodium carbonate
  2. stirringthe bi-phasic mixture was stirred for 20 minutes
  3. customThe bi-phasic mixture was transferred into a separatory funnel
  4. customthe organic phase was collected
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated down to dryness

Sources & evidence

ORD record
ord-8d49698b40674663bfd35bbc2a6991a3
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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