Diethyl Ether → 2-amino-4-(thien-2-yl)-4H-oxazol-5-one hydrochloride

HRID 1719191Notes

Reaction equation

HRID 1719191 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]([NH:8][CH:9]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[C:10]([OH:12])=[O:11])=O.CCOCC>C(#N)C>[ClH:3].[NH2:5][C:6]1[O:11][C:10](=[O:12])[CH:9]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[N:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 129116992-[(Aminocarbonyl)amino]-2-(thien-2-yl)acetic acid

Product 1

HCID 198432152-amino-4-(thien-2-yl)-4H-oxazol-5-one hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thionyl chloride (0.87 g, 7.3 mmol) was added to a suspension of 2-[(aminocarbonyl)amino]-2-(thien-2-yl)acetic acid (0.60 g, 3 mmol) in dry acetonitrile (17 ml) at 0°-5° C. under a nitrogen atmosphere. After 5 minutes dry ether (29 ml) was added and the resulting slurry was stirred for 10 minutes. The precipitate was then filtered under nitrogen, and washed well with ether. The product was dried in vacuo to afford 2-amino-4-(thien-2-yl)-4H-oxazol-5-one hydrochloride (0.60 g, 92%) as a salmon pink powder; νmax (Nujol) 1878, 1745, 1725 cm-1.

Workup

  1. filtrationThe precipitate was then filtered under nitrogen
  2. washwashed well with ether
  3. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-d9495a215b5341e0995f24c87e32e7ac
Source dataset
uspto-grants-1985_09
Patent number
US04539149

Reaction notes

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