Benzo-1,3-dioxole-5-acetic acid → [2-[(E)-[[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono]methyl]phenyl] 4-(trifluoromethyl)benzenesulfonate

HRID 1795104Notes

Reaction equation

HRID 1795104 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=[N:20][NH2:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([CH2:33][C:34](O)=[O:35])=[CH:32][C:27]=2[O:26][CH2:25]1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[N:20]/[NH:21][C:34](=[O:35])[CH2:33][C:31]2[CH:30]=[CH:29][C:28]3[O:24][CH2:25][O:26][C:27]=3[CH:32]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 738686872-[Hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonate

Product 1

HCID 11443535[2-[(E)-[[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono]methyl]phenyl] 4-(trifluoromethyl)benzenesulfonate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonate (150 mg, 0.44 mmol) and 1,3-benzodioxol-5-ylacetic acid (1.2 equiv) in DMF (1 mL) is treated with a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (167 mg, 0.87 mmol) and 4-dimethylaminopyridine (DMAP) (106 mg, 0.87 mmol) in CH2Cl2 (10 mL). The solution is shaken overnight on an orbital shaker. The solution is evaporated to dryness using a speed. Water is added to the mixture, which is then sonicated to give a solid. The solid is filtered and washed with a large amount of water. A small amount of methanol is added and the mixture sonicated. The resulting solid is filtered and washed with more methanol to yield pure 2-((E)-{2-[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono}methyl)phenyl 4-(trifluoromethyl)benzenesulfonate. The yield is 169 mg, 77%. 1H NMR (400 MHz, DMSO) □ 11.48 (2s, 1H), 8.01 (m, 6H), 7.12 (m, 6H), 5.99 (2s, 2H), 3.62 (2s, 2H). ESI− for C23H17F3N2O6S, m/z 505, (M−H)−.

Workup

  1. customThe solution is evaporated to dryness
  2. additionWater is added to the mixture, which
  3. customis then sonicated
  4. customto give a solid
  5. filtrationThe solid is filtered
  6. washwashed with a large amount of water
  7. additionA small amount of methanol is added
  8. customthe mixture sonicated
  9. filtrationThe resulting solid is filtered
  10. washwashed with more methanol

Sources & evidence

ORD record
ord-4ffdc974155346f6923c61c5c40a4930
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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