Ethanol → HCID 20084333, compound

HRID 327561Notes

Reaction equation

HRID 327561 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=2[CH3:20])[S:7][CH:8]=1)[CH3:3].O.O.[Sn](Cl)Cl.C(O)C>[OH-].[Na+]>[CH3:20][C:12]1[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:11]=1/[CH:10]=[CH:9]/[C:6]1[S:7][CH:8]=[C:4]([CH:2]([CH3:3])[CH3:1])[N:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 20084373HCID 20084373, compound

Product 1

HCID 20084333HCID 20084333, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.2 g of (E)-4-(1-methylethyl)-2-[2-(2-methyl-5-nitrophenyl)ethenyl]thiazole, 3.2 g of tin(II) chloride dihydrate and 50 ml of ethyl alcohol was heated to reflux for 2 hr. The reaction mixture was cooled in an ice bath and then diluted with 50 ml of 3N sodium hydroxide. This mixture was extracted with ethyl acetate, dried (MgSO4) and condensed in vacuo to yield 1.2 g of (E)-4-methyl-3-[2-[4-(1-methylethyl)-2-thiazolyl]ethenyl]benzenamine; m.p. 60°-61° C. from hexane.

Workup

  1. temperatureto reflux for 2 hr
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. extractionThis mixture was extracted with ethyl acetate
  4. customdried
  5. custom(MgSO4) and condensed in vacuo

Sources & evidence

ORD record
ord-855e5f17e1354dd6b149235063edaefc
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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