(Diethylamino)sulfur trifluoride → HCID 59699468, compound

HRID 2234763Notes

Reaction equation

HRID 2234763 reaction equation
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=O)=[CH:10][CH:9]=2)[O:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4]1.C(N(S(F)(F)[F:29])CC)C>ClCCl>[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH2:16][F:29])=[CH:10][CH:9]=2)[O:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59699464HCID 59699464, compound

Product 1

HCID 59699468HCID 59699468, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 20 (390.9 g, 1.11 mol) and SbCl3 (7.62 g, 0.0334 mol) in anhydrous dichloromethane (2.27 L) at −15° C., diethylamino sulfurtrifluoride (DAST) (258 ml, 2.0 mol) was added drop-wise. The reaction mixture was stirred for 3 hours at −20° C. and then allowed to warm up to room temperature overnight. The reaction was quenched with 1N NaOH solution until pH 3-4 at −20° C., and then solid NaHCO3 was added to pH=8. The organic layer was separated and the aqueous solution was extracted with dichloromethane. The combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated to provide 330 g of the desired product as a brown oil.

Workup

  1. temperatureto warm up to room temperature overnight
  2. customThe reaction was quenched with 1N NaOH solution until pH 3-4 at −20° C.
  3. additionsolid NaHCO3 was added to pH=8
  4. customThe organic layer was separated
  5. extractionthe aqueous solution was extracted with dichloromethane
  6. washThe combined organic extracts were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5e36c82a38bb4b8bb9d46ed618d0dee9
Source dataset
uspto-grants-2010_05
Patent number
US07713950B2

Reaction notes

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