Water → HCID 752274, compound

HRID 1019163Notes

Reaction equation

HRID 1019163 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:23]1([C:29](=[N:31]O)[NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C>[CH2:7]([C:8]1[O:10][N:31]=[C:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:30]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 999Phenylacetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 69186N'-Hydroxybenzenecarboximidamide

Product 1

HCID 752274HCID 752274, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenylacetic acid (2.04 g) in 50 mL of DMF was added carbonyldiimidazole (2.7 g). The mixture was stirred for 20 min and then benzene amidoxime (2.04 g) was added. The resulting mixture was stirred for 20 min at r.t. and 18 h at 75 ° C. After cooling, the reaction mixture was poured in to 50 mL of water and extracted with 2×50 mL of 1:1 hexane/EtOAc. The extract was dried over MgSO4 and filtered. The filtrate was concentrated and the residue was purified by silica gel chromatography, eluting with 1:5 EtOAc/hexane to give 2 g of the title compound as a yellow syrup.

Workup

  1. stirringThe resulting mixture was stirred for 20 min at r.t. and 18 h at 75 ° C
  2. temperatureAfter cooling
  3. extractionextracted with 2×50 mL of 1:1 hexane/EtOAc
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 1:5 EtOAc/hexane

Sources & evidence

ORD record
ord-10da1d94ec36473c9c5bd09db5c514f3
Source dataset
uspto-grants-2002_11
Patent number
US06486142B2

Reaction notes

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