Sodium Hydroxide → (E)-3-[2-[2-Cyclobutyl-4-thiazolyl]ethenyl]phenylamine

HRID 1609334Notes

Reaction equation

HRID 1609334 reaction equation
[CH:1]1([C:5]2[S:6][CH:7]=[C:8](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[CH:1]1([C:5]2[S:6][CH:7]=[C:8](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 20084352(E)-2-cyclobutyl-4-[2-(3-nitrophenyl)ethenyl]thiazole

Product 1

HCID 20084338(E)-3-[2-[2-Cyclobutyl-4-thiazolyl]ethenyl]phenylamineYield 111.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.3 g of (E)-2-cyclobutyl-4-[2-(3-nitrophenyl)ethenyl]thiazole, 0.9 g of tin(II) chloride dihydrate and 50 ml of ethyl alcohol was heated to reflux for 16 hr. The mixture was then diluted with ice water and an excess of 3N sodium hydroxide. This mixture was extracted with methylene chloride and the combined extracts were washed with water followed with brine and then dried (MgSO4). Condensation in vacuo yielded 0.3 g of (E)-3-[2-[2-Cyclobutyl-4-thiazolyl]ethenyl]phenylamine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hr
  3. extractionThis mixture was extracted with methylene chloride
  4. washthe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customCondensation in vacuo

Sources & evidence

ORD record
ord-7fe0912d5d5643e49c1999f85811f046
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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