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Methanol → 2-(2-Aminothiazol-4yl)-2-n-butoxyiminoacetic acid

HRID 364469
Notes
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Reaction equation

HRID 364469 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([O:10]CC)=[O:9])[N:6]=1.CO.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([OH:10])=[O:9])[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54097425Ethyl 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetate

Product 1

HCID 540243022-(2-Aminothiazol-4yl)-2-n-butoxyiminoacetic acidYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetate (syn isomer, 36 g.), methanol (133 ml.), tetrahydrofuran (133 ml.) and 2N aqueous solution of sodium hydroxide (133 ml.) was stirred at 30° C. for 5 hours. After the resultant solution was concentrated in vacuo, the residue was dissolved in water. The solution was adjusted to pH 7 with 10% hydrochloric acid and treated with activated charcoal. The solution was adjusted to pH 2.0 with 10% hydrochloric acid and stirred for 20 minutes under ice cooling. The precipitates were collected by filtration, washed with water and acetone in turn, and dried to give 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetic acid (syn isomer, 25.4 g.).

Workup

  1. concentrationAfter the resultant solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. additiontreated with activated charcoal
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water and acetone in turn
  6. customdried

Sources & evidence

ORD record
ord-08d2d647bd744c97bd619e8c17fadef7
Source dataset
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04604456

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes