(Diethylamino)sulfur trifluoride → HCID 67503212, compound

HRID 661371Notes

Reaction equation

HRID 661371 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:4]([C:9]2(O)[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.CCN(S(F)(F)F)CC>C(Cl)Cl>[O:13]1[C:12]2([CH2:17][CH2:18][C:9]([C:4]3[C:3]([C:2]([F:20])([F:1])[F:21])=[CH:8][CH:7]=[CH:6][N:5]=3)=[CH:10][CH2:11]2)[O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67500231HCID 67500231, compound

Product 1

HCID 67503212HCID 67503212, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of Example 36A (1.2 g, 3.96 mmol) in CH2Cl2 (25 mL) was added DAST (0.97 g, 0.76 mL, 5.75 mmol) and the reaction mixture was allowed to warm to ambient temperature. The mixture was quenched with water, diluted with EtOAc, and washed with water. Organic layer was separated, concentrated and chromatographed on silica gel (EtOAc-hexane, 0%-30%) to obtain the title compound (0.9 g, 80%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.78 (m, 1H), 8.17 (dd, J=1.6, 8.2, 1H), 7.51 (m, 1H), 5.56 (m, 1H), 3.92 (s, 4H), 2.35 (m, 3H), 1.94 (dd, J=9.1, 16.3, 1H), 1.80 (t, J=6.5, 2H). MS (DCI) m/z 286 (M+H)+.

Workup

  1. customThe mixture was quenched with water
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. customOrganic layer was separated
  5. concentrationconcentrated
  6. customchromatographed on silica gel (EtOAc-hexane, 0%-30%)

Sources & evidence

ORD record
ord-eb1277b4dcaa45ac9bea0d2f0b74c15d
Source dataset
uspto-grants-2011_12
Patent number
US08084616B2

Reaction notes

Loading…