Triethylamine → HCID 178463435, compound

HRID 871843Notes

Reaction equation

HRID 871843 reaction equation
[Cl:1][C:2]1([C:11]([OH:13])=O)[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[CH:5]=[CH:4][NH:3]1.C(N(CC)CC)C.N1C(F)=NC(F)=NC=1[F:23]>ClCCl>[Cl:1][C:2]1([C:11]([F:23])=[O:13])[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[CH:5]=[CH:4][NH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12664Cyanuric fluorideHCID 178463436HCID 178463436, compound

Product 1

HCID 178463435HCID 178463435, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 7.0 g (34.72 mmol) of acid prepared in step 2.4 and 5.32 mL (38.19 mmol) of triethylamine in 98 mL of dichloromethane are added 5.89 mL (69.79 mmol) of cyanuric fluoride. The mixture is stirred for 3 hours and the solution is diluted with 590 mL of CH2Cl2 and 190 mL of ice-cold aqueous NaHCO3. The organic phase is washed twice with 190 mL of ice-cold aqueous NaHCO3 and dried over MgSO4. The solvent is then evaporated off under reduced pressure. 7.0 g of expected product are obtained in the form of a red oil that solidifies slowly, and that is used as obtained in the following step. Quantitative yield.

Workup

  1. washThe organic phase is washed twice with 190 mL of ice-cold aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. customThe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record
ord-13d9bf1268aa4609918dae841d0658fc
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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