Ammonia → HCID 178448400, compound

HRID 1168016Notes

Reaction equation

HRID 1168016 reaction equation
[Cl-].[C:2]([IH+:6]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:5])([CH3:4])[CH3:3].C([O-])([O-])(OCC)CC.[F:25][C:26]([F:32])([F:31])[S:27]([OH:30])(=[O:29])=[O:28].N>C(Cl)Cl>[O-:30][S:27]([C:26]([F:32])([F:31])[F:25])(=[O:29])=[O:28].[C:13]([IH+:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 62406Trifluoromethanesulfonic acidHCID 86600181Ethyl ortho-propionateHCID 178448397HCID 178448397, compound

Product 1

HCID 178448400HCID 178448400, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butylphenyliodonium chloride (443 mg; 1 mmol), ethyl orthopropionate (211 mg; 1.5 mmol), and trifluoromethanesulfonic acid (165 mg; 1.1 mmol) were dissolved in anhydrous methylene chloride (10 ml), and the resultant mixture was stirred for 2 hours at room temperature. The reaction mixture was alkalinized by adding 1% aqueous ammonia (10 ml), and extracted with methylene chloride twice, followed by drying. The solvent was evaporated, and the thus-obtained solid matter was washed with ether, to thereby yield 491 mg of the target compound as white crystals (yield: 91%).

Workup

  1. extractionextracted with methylene chloride twice
  2. customby drying
  3. customThe solvent was evaporated
  4. washthe thus-obtained solid matter was washed with ether

Sources & evidence

ORD record
ord-f94d426807034e67953ed2499dc0e4c8
Source dataset
uspto-grants-2003_09
Patent number
US06620957B1

Reaction notes

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