Triethylamine → Trifludimoxazin

HRID 405686Notes

Reaction equation

HRID 405686 reaction equation
CNC(NC)=[S:4].C(N(CC)CC)C.[F:14][C:15]1([F:33])[O:20][C:19]2[CH:21]=[C:22]([F:28])[C:23]([N:25]=[C:26]=[O:27])=[CH:24][C:18]=2[N:17]([CH2:29][C:30]#[CH:31])[C:16]1=[O:32].[C:34](N1C=CN=C1)([N:36]1[CH:40]=[CH:39][N:38]=[CH:37]1)=[O:35]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:39][N:38]1[C:37](=[S:4])[N:36]([CH3:40])[C:34](=[O:35])[N:25]([C:23]2[C:22]([F:28])=[CH:21][C:19]3[O:20][C:15]([F:14])([F:33])[C:16](=[O:32])[N:17]([CH2:29][C:30]#[CH:31])[C:18]=3[CH:24]=2)[C:26]1=[O:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2723631N,N'-DimethylthioureaHCID 866643002,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 49831143Trifludimoxazin

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
80 °C

Procedure

To 1,3-dimethylthiourea (2.489 g, 23.89 mmol) and triethylamine (2.78 ml, 19.91 mmol) in dry toluene was added 2,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (5.62 g, 19.91 mmol) in dry toluene. Hereto was subsequently added carbonyldiimidazole (CDI; 6.46 g, 39.8 mmol) and the resulting mixture was stirred at 80° C. overnight. Then the reaction mixture was cooled to room temperature and poured into ethyl acetate/water under stirring. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined extracts were washed with brine, dried with Na2SO4 and concentrated to yield 14.4 g.

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. stirringunder stirring
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customto yield 14.4 g

Sources & evidence

ORD record
ord-dad3d3b56d2343c5b9ec6f5b7e1c341f
Source dataset
uspto-grants-2014_06
Patent number
US08754008B2

Reaction notes

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