(Diethylamino)sulfur trifluoride → HCID 67499172, compound

HRID 2197581Notes

Reaction equation

HRID 2197581 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2(O)[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(S(F)(F)[F:25])CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:8]2([F:25])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67499969HCID 67499969, compound

Product 1

HCID 67499172HCID 67499172, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of the product of Example 1A (7.13 g, 26.4 mmol) in CH2Cl2 (120 mL) was added diethylaminosulfur trifluoride (DAST, 6.0 g, 4.89 mL, 37.0 mmol). The reaction mixture was allowed to warm to ambient temperature, quenched with water, diluted with ethyl acetate, and washed with water. The organic layer was separated and concentrated. The resulting residue was chromatographed on silica gel, eluting with 0%-30% ethyl acetate-hexane to obtain the title compound (3.0 g, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.69-1.77 (m, 2H), 1.86 (td, J=12.89, 4.75 Hz, 2H), 2.15-2.40 (m, 4H), 3.91 (s, 4H), 7.44 (ddd, J=8.14, 4.75, 0.68 Hz, 1H), 7.96 (dd, J=7.97, 1.53 Hz, 1H), 8.52 (dt, J=4.75, 1.19 Hz, 1H). MS (DCI) m/z 272.05 (M+H)+.

Workup

  1. customquenched with water
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed on silica gel
  7. washeluting with 0%-30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-b7655bb42bd44ad9a5c83e5e2a8d3f35
Source dataset
uspto-grants-2012_12
Patent number
US08338603B2

Reaction notes

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