1,1'-Carbonyldiimidazole → (NZ)-N-[3-(4-chlorophenyl)-1,3-thiazolidin-2-ylidene]imidazole-1-carboxamide

HRID 390698

Reaction equation

HRID 390698 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][S:10]/[C:9]/2=[N:13]\[H])=[CH:4][CH:3]=1.[C:15](N1C=CN=C1)([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[O:16]>O1CCCC1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][S:10]/[C:9]/2=[N:13]\[C:15]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178506456HCID 178506456, compound

Product 1

HCID 87449094(NZ)-N-[3-(4-chlorophenyl)-1,3-thiazolidin-2-ylidene]imidazole-1-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2Z)-3-(4-Chlorophenyl)-1,3-thiazolidin-2-imine (233 mg, 1.095 mmol, Example 24A) and carbonyldiimidazole (195 mg, 1.205 mmol) in dry tetrahydrofuran were heated at 65° C. After 14 hours the reaction mixture cooled down, diluted with 75 mL of dichloromethane, and washed successively with sodium bicarbonate (50 mL) water and brine (50 mL), dried over magnesium sulfate and concentrated under reduced pressure to give the title compound.

Workup

  1. temperatureAfter 14 hours the reaction mixture cooled down
  2. washwashed successively with sodium bicarbonate (50 mL) water and brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-261ba4af212b4acca6e31cb6a1bd37a4
Source dataset
uspto-grants-2013_02
Patent number
US08383657B2

Linked notes

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