1,1'-Carbonyldiimidazole → 3-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-one

HRID 1528343Notes

Reaction equation

HRID 1528343 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)\[C:11](=[N:13]\[OH:14])\[NH2:12])[N:6]=1.C1N=CN([C:26](N2C=NC=C2)=[O:27])C=1>CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)\[C:11]2[NH:12][C:26](=[O:27])[O:14][N:13]=2)[N:6]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 136626361(2Z)-2-[(2-amino-1,3-thiazol-4-yl)methoxyimino]-N'-hydroxy-2-phenylethanimidamide

Product 1

HCID 1366263593-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-oneYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1Z,2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N′-hydroxy-2-phenylethanimidamide (3 g, 10.29 mmol, 1 eq.) in DMF (50 ml) was added CDI (1.66 g, 10.29 mmol, 1 eq.) and stirring at room temperature was allowed for 30 min before heated to 80° C. for 6 h. The reaction was quenched by addition of water and extracted with EtOAc (3×50 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated. The residue was triturated in MeCN and a white solid was isolated by filtration giving 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-1,2,4-oxadiazol-5(4H)-one (2.89 g, 50% purity, 43% yield).

Workup

  1. temperaturebefore heated to 80° C. for 6 h
  2. customThe reaction was quenched by addition of water
  3. extractionextracted with EtOAc (3×50 ml)
  4. washwashed with aq. sat. NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was triturated in MeCN
  8. customa white solid was isolated by filtration

Sources & evidence

ORD record
ord-342e384051334fdaa58d71568c24bbc1
Source dataset
uspto-grants-2015_07
Patent number
US09090600B2

Reaction notes

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