(Diethylamino)sulfur trifluoride → HCID 59699468, compound

HRID 901083Notes

Reaction equation

HRID 901083 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-67be831b45aa455f810b4e65e57d149c
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Reaction notes

Loading…