Methanol → 2-(2-Amino-4-thiazolyl)-2-propoxyiminoacetic acid

HRID 2295543Notes

Reaction equation

HRID 2295543 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][CH3:17])[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][CH3:17])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53867037Ethyl 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetate

Product 1

HCID 540960402-(2-Amino-4-thiazolyl)-2-propoxyiminoacetic acidYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetate (syn isomer, 10 g.) in a mixture of tetrahydrofuran (39 ml.), methanol (39 ml.) and 1 N sodium hydroxide (75.8 ml.) was stirred at 35° to 40° C. for 5 hours. After the resultant solution was concentrated under reduced pressure, the aqueous residue was adjusted to pH 2.5 with 10% hydrochloric acid. The precipitates were collected by filtration and dried to give 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetic acid (syn isomer, 6.2 g.), mp 161° C. (dec.)

Workup

  1. concentrationAfter the resultant solution was concentrated under reduced pressure
  2. filtrationThe precipitates were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-3a2a07c8d7294243ae19332216dc2abb
Source dataset
uspto-grants-1984_01
Patent number
US04425341

Reaction notes

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