(Diethylamino)sulfur trifluoride → HCID 67503212, compound

HRID 2197599Notes

Reaction equation

HRID 2197599 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-d8ebc1c7078e4e8c8e3462190a087b4b
Source dataset
uspto-grants-2012_12
Patent number
US08338603B2

Reaction notes

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