Dichloromethane → HCID 9884191, compound

HRID 1108561Notes

Reaction equation

HRID 1108561 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH2:18][CH:17]([CH2:19][NH:20][C:21](=O)[CH3:22])[O:16][N:15]=2)[CH:5]=[C:6]([F:13])[C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:33]2)=CC=1.C(Cl)Cl>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH2:18][CH:17]([CH2:19][NH:20][C:21](=[S:33])[CH3:22])[O:16][N:15]=2)[CH:5]=[C:6]([F:13])[C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 87949Lawesson's reagentHCID 9948972HCID 9948972, compound

Product 1

HCID 9884191HCID 9884191, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the final product of Example 28 (150 mg) and [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's Reagent) (189 mg) in 1,4-dioxane (5 mL) is heated at reflux for 1.5 hours and stirred at ambient temperature. After 18 hours, TLC analysis (5% CH3 0H--CH2Cl2) indicated the reaction to be complete. The mixture is diluted with water (50 mL), extracted with EtOAc (3×25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to a light yellow solid. The crude material is recrystallized from 5%CH3OH/EtOAc to give 119 mg of the title compound as a white solid, mp 238-240° C. dec and MS(ES) 337 (M+H)+ [α]25D.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customthe reaction
  3. extractionextracted with EtOAc (3×25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a light yellow solid
  7. customThe crude material is recrystallized from 5%CH3OH/EtOAc

Sources & evidence

ORD record
ord-654fd28230c94a3fb703899191da5b9a
Source dataset
uspto-grants-2000_05
Patent number
US06069141

Reaction notes

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