Acetic Anhydride → 2-(2-Formamidothiazol-4-yl)-2-propoxyiminoacetic acid

HRID 1905155Notes

Reaction equation

HRID 1905155 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:11][O:12][CH2:13][CH2:14][CH3:15])[C:8]([OH:10])=[O:9])[N:6]=1.[C:16](OC(=O)C)(=[O:18])C>C(O)=O>[CH:16]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:11][O:12][CH2:13][CH2:14][CH3:15])[C:8]([OH:10])=[O:9])[N:6]=1)=[O:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 540960402-(2-Amino-4-thiazolyl)-2-propoxyiminoacetic acid

Product 1

HCID 536876672-(2-Formamidothiazol-4-yl)-2-propoxyiminoacetic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N.M.R. δppm (DMSO-d6): 0.89 (3H, t, J=7 Hz), 1.63 (2H, sextet, J=7 Hz), 4.05 (2H, t, J=7 Hz), 6.83 (1H, s), 6.9-8.8 (3H, broad). (5) 2-(2-Aminothiazol-4-yl)-2-n-propoxyiminoacetic acid (syn isomer, 21.8 g.), acetic anhydride (38.8 g.) and formic acid (17.5 g.) were treated in a similar manner to that of Example F-(5), and then the obtained oil was triturated with diisopropyl ether to give 2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetic acid (syn isomer, 19.2 g.), mp. 164° C. (dec.).

Workup

  1. customthe obtained oil was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-e9d12495a79e41aa8c3c22e3575f7c03
Source dataset
uspto-grants-1989_06
Patent number
US04841062

Reaction notes

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