3-Nitrobenzaldehyde → 4-Isopropyl-2-(trans-3-nitrostyryl)thiazole

HRID 1199693Notes

Reaction equation

HRID 1199693 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O)([O-:10])=[O:9].[CH:19]([C:22]1[N:23]=[C:24]([CH3:27])[S:25][CH:26]=1)([CH3:21])[CH3:20]>>[CH:19]([C:22]1[N:23]=[C:24](/[CH:27]=[CH:14]/[C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=2)[S:25][CH:26]=1)([CH3:21])[CH3:20]

Participants

4

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 7918Acetic AnhydrideHCID 5205692-Methyl-4-(1-methylethyl)thiazole

Product 1

HCID 157183584-Isopropyl-2-(trans-3-nitrostyryl)thiazoleYield 32%

Procedure

To 11.3 ml of acetic anhydride were added 29.0 g of 3-nitrobenzaldehyde and 27.1 g of 4-isopropyl-2-methylthiazole and the reaction was carried out under nitrogen gas stream at 170° C. for 23 hours. After completion of the reaction, low boiling materials were evaporated under reduced pressure and the residue was recrystallized from ethyl ether-n-hexane to give 16.8 g (yield 32%) of the title compound as yellowish white crystals.

Workup

  1. customat 170° C.
  2. customfor 23 hours
  3. customAfter completion of the reaction, low boiling materials
  4. customwere evaporated under reduced pressure
  5. customthe residue was recrystallized from ethyl ether-n-hexane

Sources & evidence

ORD record
ord-37b0ac1afc514b0aa30310eae7c1b74b
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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