(Diethylamino)sulfur trifluoride → HCID 59822033, compound

HRID 1645321Notes

Reaction equation

HRID 1645321 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Si:10]([O:17][C@H:18]1[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][C:24]2[N:23]=[C:22]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:21]([C@H:35]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)O)=[C:20]([CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)[C:19]1=2)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Si:10]([O:17][C@H:18]1[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][C:24]2[N:23]=[C:22]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:21]([C@@H:35]([F:7])[C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:44])([F:46])[F:45])=[CH:41][CH:42]=3)=[C:20]([CH:47]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]3)[C:19]1=2)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 59822022HCID 59822022, compound

Product 1

HCID 59822033HCID 59822033, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At −55° C. and under argon, 3.21 ml of diethylaminosulphur trifluoride (24.3 mmol, 1.5 eq.) are added dropwise to a solution of 9.96 g (16.2 mmol) of the compound from Example 5A in 300 ml of dry toluene. The mixture is stirred at this temperature for 1 h and then at room temperature for a further 2 h. For work-up, 120 ml of a saturated sodium bicarbonate solution are added carefully. The mixture is extracted three times in total with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product is purified by filtration through silica gel (mobile phase: cyclohexane/ethyl acetate 9:1).

Workup

  1. waitat room temperature for a further 2 h
  2. extractionThe mixture is extracted three times in total with ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe crude product is purified by filtration through silica gel (mobile phase: cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-6e38bf60b3d74a68b9957d87dd73e703
Source dataset
uspto-grants-2012_02
Patent number
US08124775B2

Reaction notes

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