1,1'-Carbonyldiimidazole → HCID 59323900, compound

HRID 1715176Notes

Reaction equation

HRID 1715176 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1.[CH:17]1[N:21]=[CH:20][N:19]([C:22](N2C=NC=C2)=[O:23])[CH:18]=1>C1COCC1.C(Cl)Cl>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:4]2[S:3][C:2]([NH:1][C:22]([N:19]3[CH:18]=[CH:17][N:21]=[CH:20]3)=[O:23])=[N:6][C:5]=2[CH3:7])=[CH:9][CH:10]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59383111HCID 59383111, compound

Product 1

HCID 59323900HCID 59323900, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-[4-(2-amino-4-methyl-thiazol-5-yl)-phenyl]-ethanone (0.57 g, 2.45 mmol) is dissolved in a mixture of THF (10 ml) and DCM (20 ml) and heated in an oil bath set to 50° C. CDI is added (0.64 g, 3.92 mmol) and the reaction mixture heated at 50° C. for a further 2 hours in which a pale yellow precipitate forms. After cooling to room temperature the precipitate is filtered, washed with DCM and dried under high vacuum to yield the title compound.

Workup

  1. temperatureheated in an oil bath
  2. customset to 50° C
  3. temperatureAfter cooling to room temperature the precipitate
  4. filtrationis filtered
  5. washwashed with DCM
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-2f88cfa5bf084414b3c5eb2095768c78
Source dataset
uspto-grants-2010_09
Patent number
US07799810B2

Reaction notes

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