Triethylamine → HCID 9932116, compound

HRID 617208Notes

Reaction equation

HRID 617208 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[O:13]=[C:14]1[NH:18][C:17](=[O:19])[CH:16]([C:20]2[CH:21]=[CH:22][C:23]([O:29][CH3:30])=[C:24]([CH:28]=2)[C:25](O)=[O:26])[S:15]1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C=O)C.O>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:25](=[O:26])[C:24]2[CH:28]=[C:20]([CH:16]3[S:15][C:14](=[O:13])[NH:18][C:17]3=[O:19])[CH:21]=[CH:22][C:23]=2[O:29][CH3:30])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 768044-(Trifluoromethyl)benzylamineHCID 11129275HCID 11129275, compound

Product 1

HCID 9932116HCID 9932116, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-trifluoromethylbenzylamine (71.9 g) in DMF (1 L) were added 5-(2,4-dioxothiazolidin-5-yl)-2-methoxybenzoic acid (98.7 g), diethyl cyanophosphate (94.7 g) and triethylamine (63 ml) under cooling with ice and stirring, and the mixture was stirred for 15 minutes as it was. Thereafter, it was stirred for 7 hours at room temperature. The reaction mixture was poured into water, which was extracted with ethyl acetate and, after washing with water, dried over anhydrous sodium sulfate. This was concentrated under reduced pressure and the residue was dissolved into ethanol. After treating with activated charcoal, this was filtered through celite and water was added to the filtrate. The crystals deposited were collected by filtration and dried to obtain 83.6 g (53%) of aimed compound as colorless powder. Melting point: 168.0~169.0° C.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 15 minutes as it
  3. stirringThereafter, it was stirred for 7 hours at room temperature
  4. extractionwas extracted with ethyl acetate
  5. washafter washing with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThis was concentrated under reduced pressure
  8. dissolutionthe residue was dissolved into ethanol
  9. additionAfter treating with activated charcoal
  10. filtrationthis was filtered through celite and water
  11. additionwas added to the filtrate
  12. filtrationThe crystals deposited were collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-d4c86025b4dc4c89abecf813173c4f8e
Source dataset
uspto-grants-1999_09
Patent number
US05948803

Reaction notes

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