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

HRID 1659774Notes

Reaction equation

HRID 1659774 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-c3302fe4884c4138a0dbb46d5a8da0b3
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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