Sodium Hydroxide → 5-(4-Methoxyphenyl)-4-methyl-2-thiazolamine

HRID 1092947Notes

Reaction equation

HRID 1092947 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([NH:16]C(=O)C)=[N:13][C:12]=2[CH3:20])=[CH:7][CH:6]=1.[OH-].[Na+]>O.C(O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:15][C:14]([NH2:16])=[N:13][C:12]=2[CH3:20])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21225539hydrochloric acid HClHCID 85861728HCID 85861728, compound

Product 1

HCID 282765965-(4-Methoxyphenyl)-4-methyl-2-thiazolamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of concentrated hydrochloric acid HCl (20 ml) in water (30 ml) is added to N-[5-(4-Methoxy-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 28a) (2 g, 7.63 mmol) in ethanol. After 5 hours at reflux, the reaction is poured into water (600 ml) and the pH is adjusted to 9/10 with 2.5 M NaOH. The aqueous layer is then extracted with ethyl acetate (3×200 ml). The combined organic layers are dried over MgSO4, filtered and concentrated to afford 5-(4-Methoxy-phenyl)-4-methyl-thiazol-2-ylamine.

Workup

  1. temperatureAfter 5 hours at reflux
  2. extractionThe aqueous layer is then extracted with ethyl acetate (3×200 ml)
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-71c35244045e4a13a50ae4176b9adcc0
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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