Diisopropyl Ether → 2-(2-Formamidothiazol-4-yl)-2-(propargyloxyimino)acetic acid

HRID 2412778Notes

Reaction equation

HRID 2412778 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH2:8]([O:11][N:12]=[C:13]([C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1)[C:14]([OH:16])=[O:15])[C:9]#[CH:10].C(OC(C)C)(C)C>C(O)=O>[CH2:8]([O:11][N:12]=[C:13]([C:17]1[N:18]=[C:19]([NH:22][CH:1]=[O:3])[S:20][CH:21]=1)[C:14]([OH:16])=[O:15])[C:9]#[CH:10]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 543726822-(2-Aminothiazol-4-yl)-2-propargyloxyiminoacetic acid

Product 1

HCID 537194582-(2-Formamidothiazol-4-yl)-2-(propargyloxyimino)acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Formic acid (107 g.) was added to acetic anhydride (239 g.) under ice-cooling, and the mixture was stirred for 1 hour at 50° C. and then cooled to 20° C. To the mixture was added 2-(2-propynyloxyimino)-2-(2-aminothiazol-4-yl)acetic acid (syn isomer) (135 g.), and the mixture was stirred for 3 hours at ambient temperature. To the mixture was added diisopropyl ether (400 ml.) and then the precipitated crystals were collected by filtration, washed with diisopropyl ether and then dried to give 2-(2-propynyloxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (118.4 g.).

Workup

  1. temperaturecooling
  2. temperaturecooled to 20° C
  3. stirringthe mixture was stirred for 3 hours at ambient temperature
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with diisopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-a3051cec8bd64b6c9fe14a838b6feab2
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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