Benzene → HCID 19090524, compound

HRID 1463534Notes

Reaction equation

HRID 1463534 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:9])[O:7][C:6](C(O)=O)=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C1C=CC=CC=1.[F:45][C:46]1[CH:52]=[C:51]([F:53])[CH:50]=[CH:49][C:47]=1[NH2:48].C([N:56]([CH2:59]C)CC)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:9])[O:7][C:6]([NH:56][C:59]([NH:48][C:47]1[CH:49]=[CH:50][C:51]([F:53])=[CH:52][C:46]=1[F:45])=[O:29])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 103800926-chloro-4-phenylisocoumarin-3-carboxylic Acid

Product 1

HCID 19090524HCID 19090524, compound

Procedure

To a mixture of 6-chloro-4-phenylisocoumarin-3-carboxylic acid (1.50 g), diphenyl phosphoryl azide (DPPA) (1.43 ml) and benzene (50 ml) was added dropwise triethylamine (0.71 ml) while stirring at room temperature. This mixture was stirred for one hour at room temperature and for 30 minutes under reflux, then there was added 2,4-difluoroaniline (0.80 ml), followed by refluxing for 2 hours. The reaction mixture was cooled, and then washed with water, diluted hdyrochloric acid, an aqueous solution of sodium hydrogencarbonate and water, successively, then dried (Na2SO4), followed by distilling off the solvent. The residue was subjected to a silica gel column chromatography (hexane-acetone=4:1) to afford the above-titled compound as colorless crystals (0.90 g).

Workup

  1. stirringThis mixture was stirred for one hour at room temperature and for 30 minutes
  2. temperatureunder reflux
  3. temperatureby refluxing for 2 hours
  4. temperatureThe reaction mixture was cooled
  5. washwashed with water
  6. additiondiluted hdyrochloric acid
  7. dry with materialan aqueous solution of sodium hydrogencarbonate and water, successively, then dried (Na2SO4)
  8. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-3efe1cfade69465597bb7d9aa1edb940
Source dataset
uspto-grants-1994_04
Patent number
US05300646

Reaction notes

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