Sodium Hydroxide → (E)-2-[2-(5-amino-2-chlorophenyl)ethenyl]-4-(1-methylethyl)thiazole

HRID 1609327Notes

Reaction equation

HRID 1609327 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1/[CH:11]=[CH:12]/[C:13]1[S:14][CH:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3](/[CH:11]=[CH:12]/[C:13]2[S:14][CH:15]=[C:16]([CH:18]([CH3:19])[CH3:20])[N:17]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 20084355(E)-2-[2-(2-chloro-5-nitrophenyl)ethenyl]-4-(1-methylethyl)thiazole

Product 1

HCID 20084321(E)-2-[2-(5-amino-2-chlorophenyl)ethenyl]-4-(1-methylethyl)thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution composed of 3.0 g of (E)-2-[2-(2-chloro-5-nitrophenyl)ethenyl]-4-(1-methylethyl)thiazole, 8.0 g of tin(II) chloride dihydrate and 100 ml of ethyl alcohol was heated to reflux for 1 hr. The reaction mixture was then condensed to half of its original volume, diluted with ice water, basified with 3N sodium hydroxide and extracted with methylene chloride. The combined extracts were washed with water and brine, dried (MgSO4)and condensed in vacuo to yield (E)-2-[2-(5-amino-2-chlorophenyl)ethenyl]-4-(1-methylethyl)thiazole; m.p. 82°-85° C. from hexane.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr
  3. customcondensed to half of its original volume
  4. extractionextracted with methylene chloride
  5. washThe combined extracts were washed with water and brine, dried (MgSO4)and condensed in vacuo

Sources & evidence

ORD record
ord-de5cc312a7354882bbd1cd7bf89d058c
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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