1,1'-Carbonyldiimidazole → 5-(2,4-Dichlorophenyl)-5-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 1979712Notes

Reaction equation

HRID 1979712 reaction equation
[NH2:1][CH2:2][C:3]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])([OH:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>O1CCCC1>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:3]1([CH2:4][N:5]2[CH:9]=[N:8][CH:7]=[N:6]2)[O:10][C:19](=[O:20])[NH:1][CH2:2]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 147065211-[3-Amino-2-(2,4-dichlorophenyl)-2-hydroxyprop-1-yl]-1H-1,2,4-triazole

Product 1

HCID 147065245-(2,4-Dichlorophenyl)-5-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the amine (A) (0.1 g, 0.35 mmole) and 1,1'-carbonyldiimidazole (0.056 g, 0.35 mmole) in tetrahydrofuran (5 ml) was stirred at room temperature for five hours. The solvent was then evaporated and the residue was dissolved in ethyl acetate (20 ml). This solution was washed three times with water (300 ml, total), dried (MgSO4), evaporated and the residue triturated with a mixture of 60°-80° C. petrol:ether to give, as a white solid, the title compound, 0.074 g (68%), m.p. 223° C.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washThis solution was washed three times with water (300 ml, total)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe residue triturated with a mixture of 60°-80° C. petrol
  7. customether to give, as a white solid

Sources & evidence

ORD record
ord-fa2e2dc0f2e54c2c9fd239bb6e0aa898
Source dataset
uspto-grants-1984_11
Patent number
US04482558

Reaction notes

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