2-Fluorobenzhydrazide → HCID 178427628, compound

HRID 1016412Notes

Reaction equation

HRID 1016412 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[N:10][NH:11][C:12]=1C=O.[F:26][C:27]1[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=1[C:29]([NH:31][NH2:32])=[O:30]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12](=[N:32][NH:31][C:29]([C:28]2[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=2[F:26])=[O:30])[N:11]=[N:10][C:9]=1[O:15][S:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 1362882-FluorobenzhydrazideHCID 18406860HCID 18406860, compound

Product 1

HCID 178427628HCID 178427628, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The product from step c) (10 g, 0.028 mol) was suspended in xylene (250 ml) with 2-fluorobenzoic hydrazide (4.7 g, 0.0231 mol) and heated under reflux for 3 h. After cooling, the reaction mixture was filtered and the solid produced was washed in the sinter funnel several times with dichloromethane then concentrated under vacuum to leave a solid (10.53 g). The product existed as a 1:1 mixture of 2 tautomers. 1H NMR (400 MHz, CDCl3) δ 2.37 (3H, s), 7.18-7.66 (12H, m), 8.06 (1H, s), 11.90 (0.5H, s), 13.78 (0.5H, s); MS (ES+) m/e 497 [MH]+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customthe solid produced
  6. washwas washed in the sinter funnel several times with dichloromethane
  7. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-63936a510eb44100bf3004bf3564773b
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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