Triethylamine → HCID 10365996, compound

HRID 1197888Notes

Reaction equation

HRID 1197888 reaction equation
C([N:3]([CH2:6]C)CC)C.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[C:15](C(O)=O)=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[C:13]=2[CH:29]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.[F:47][C:48]1[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:49]=1[NH2:50]>O.C1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[C:15]([NH:3][C:6]([NH:50][C:49]3[CH:51]=[CH:52][C:53]([F:55])=[CH:54][C:48]=3[F:47])=[O:37])=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[C:13]=2[CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 10335822HCID 10335822, compound

Product 1

HCID 10365996HCID 10365996, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Triethylamine (0.14ml) was dropwise added to a mixture of 6-chloro-4-(2-methylphenyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid (342 mg), diphenylphosphoryl azide (DPPA, 330 mg) and benzene (5 ml) under stirring. The mixture was stirred for 20 minutes at room temperature and for 20 minutes under reflux, to which 2,4-difluoroaniline (0.12 ml) was added and further stirred for 2 hours at room temperature. The reaction mixture to which water was added was extracted with ethyl acetate. The extract was washed with water, a saturated NaHCO3 aqueous solution and water, and then dried (MgSO4). The solvent was distilled off to obtain crystals of N-[6-chloro-4-(2-methylphenyl)-2-oxo-2H-1-benzopyran-3-yl]-N'-(2,4-difluorophenyl) urea (311 mg, 70.7%). Recrystallization from ethanol gave colorless needles of mp 210-212° C.

Workup

  1. stirringThe mixture was stirred for 20 minutes at room temperature and for 20 minutes
  2. additionwas added
  3. stirringfurther stirred for 2 hours at room temperature
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated NaHCO3 aqueous solution and water, and then dried (MgSO4)
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-329f74b595494f599eee56ae1c096135
Source dataset
uspto-grants-1994_01
Patent number
US05278186

Reaction notes

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