Succinic anhydride → (E)-4-[[3-[2-(4-cyclopropyl-2-thiazolyl)-ethenyl]phenyl]amino]-4-oxobutanoic acid

HRID 359488Notes

Reaction equation

HRID 359488 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]3[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=3)[S:7][CH:8]=2)[CH2:3][CH2:2]1.[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1.C([O-])(=O)C.[Na+]>COCCOC>[CH:1]1([C:4]2[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:14]=[CH:15][CH:16]=3)[S:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 517045Sodium AcetateHCID 15136080(E)-3-[2-[4-(cyclopropyl)-2-thiazolyl]ethenyl]benzeneamine

Product 1

HCID 15136081(E)-4-[[3-[2-(4-cyclopropyl-2-thiazolyl)-ethenyl]phenyl]amino]-4-oxobutanoic acidYield 40.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2.5 g (10 mmol) of (E)-3-[2-[4-(cyclopropyl)-2-thiazolyl]ethenyl]benzeneamine prepared as in example 1 as above, 1.5 g (15 mol) of succinic anhydride, 1.64 g (20 mmol) of anhydrous sodium acetate and 200 ml of 1,2-dimethoxyethane was stirred and heated under reflux for 2 hr. The reaction mixture was cooled and concentrated in vacuo. The residue was heated on the steam bath with 200 ml of water for 0.5 hr. The solid was collected and recrystallized from ethanol to give 1.4 g of (E)-4-[[3-[2-(4-cyclopropyl-2-thiazolyl)-ethenyl]phenyl]amino]-4-oxobutanoic acid, mp 177°-179° dec, as off-white needles.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. temperatureThe residue was heated on the steam bath with 200 ml of water for 0.5 hr
  6. customThe solid was collected
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fd436081ed814ead969bd9fd5e7c25f7
Source dataset
uspto-grants-1991_03
Patent number
US05001140

Reaction notes

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