Dimethyl Sulfoxide → HCID 45083718, compound

HRID 1647834Notes

Reaction equation

HRID 1647834 reaction equation
C[N+]1([O-])CC[O:5]CC1.CS(C)=O.Br[CH2:14][C:15]1[O:19][N:18]=[C:17]([CH:20]([C:22]#[CH:23])[OH:21])[CH:16]=1.OP([O-])(O)=O.[K+]>C(Cl)Cl>[OH:21][CH:20]([C:17]1[CH:16]=[C:15]([CH:14]=[O:5])[O:19][N:18]=1)[C:22]#[CH:23]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 82029Methyl morpholine oxideHCID 516951Monobasic potassium phosphateHCID 53965808HCID 53965808, compound

Product 1

HCID 45083718HCID 45083718, compoundYield 292.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9.8 g of 4-methyl morpholine oxide, 68 cm3 of dimethylsulphoxide and 34 cm3 of methylene chloride are added at 0° C. to a solution containing 4 g of the product prepared in Stage C and 30 cm3 of methylene chloride. The mixture is allowed to return to 20° C. and agitated for 5 hours. It is poured into an aqueous solution of potassium acid phosphate. Extraction is carried out with ethyl acetate, the extracts are dried, filtered and brought to dryness. 8.18 g of product is obtained which is chromatographed on silica, eluting with a hexane-ethyl acetate mixture (1-1). In this way 1.96 g of desired product is obtained.

Workup

  1. customto return to 20° C.
  2. extractionExtraction
  3. customthe extracts are dried
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6e2265b624cc4fa1b639fa8a4d2345e3
Source dataset
uspto-grants-1995_07
Patent number
US05434175

Reaction notes

Loading…