Diazomethane → HCID 58121052, compound

HRID 1186699Notes

Reaction equation

HRID 1186699 reaction equation
[C:1]1([C:7]2[S:8][C:9]([C:18]([OH:20])=[O:19])=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:23])=[N-]>CCOC(C)=O.CCOCC>[C:1]1([C:7]2[S:8][C:9]([C:18]([O:20][CH3:23])=[O:19])=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 71311932,4-diphenyl-1,3-thiazole-5-carboxylic Acid

Product 1

HCID 58121052HCID 58121052, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a pre-cooled (0° C.) solution of 2,4-Diphenyl-1,3-thiazole-5-carboxylic acid 72 (400 mg, 1.422 mmol) in EtOAc (7.109 ml) was added a 0.5 M solution of diazomethane (5.69 ml, 2.84 mmol) in Et2O (freshly prepared) (c.a. 5 mL) and the resulting white suspension was stirred at 0° C. for 1 h. TLC showed completion. Then, the small amount of white solid left was filtered off and the filtrate was concentrated in vacuo to afford methyl 2,4-diphenylthiazole-5-carboxylate 73 (0.449 g, 107% yield).

Workup

  1. customfreshly prepared) (c.a. 5 mL)
  2. waitThen, the small amount of white solid left
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fd061fb08bd840538ada8cb4e9cb5459
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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