Dichloromethane → HCID 21925587, compound

HRID 1243556Notes

Reaction equation

HRID 1243556 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=[O:8])=O.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(=O)([O-])O.[Na+].ClCCl>C(#N)C.O>[Cl:1][CH2:2][C:3]1[O:8][C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:11][CH2:10]2)=[N:6][N:5]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 23544062HCID 23544062, compound

Product 1

HCID 21925587HCID 21925587, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The hydrazide of Preparation 3 (50.0 g, 169 mmol) was suspended in acetonitrile (250 ml) and cooled using an ice bath. Trifluoromethanesulfonic anhydride (29.9 ml, 177 mmol) was added dropwise at T<15° C. The reaction was warmed to room temperature and stirred for 16 hours. The reaction was cooled using an ice bath and a solution of sodium hydrogen carbonate (29.8 g, 354 mmol) in water (250 ml) was added dropwise. Dichloromethane (250 ml) was added and the phases were separated. The organic containing product phase was used in preparation 14b.

Workup

  1. temperaturecooled
  2. temperatureThe reaction was cooled
  3. customthe phases were separated
  4. customThe organic containing product phase was used in preparation 14b

Sources & evidence

ORD record
ord-b537dabbe97c4c52ae8263693fc9f8e1
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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