1,1'-Carbonyldiimidazole → HCID 66616207, compound

HRID 2172162Notes

Reaction equation

HRID 2172162 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)=[S:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>ClC(Cl)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][C:24](=[O:25])[N:13]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=3)[N:12]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86624588HCID 86624588, compound

Product 1

HCID 66616207HCID 66616207, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Methyl 4-{2-[(4-isopropylphenyl)carbonothioyl]hydrazino}benzoate (0.26 g, 0.8 mmol) and carbonyldiimidazole (0.19 g, 1.2 mmol) are stirred at 80° C. in dichloroethane (20 mL) overnight, and the mixture is subjected to chromatography directly (silica gel, 4:1 ethyl acetate-hexanes) to provide methyl 4-[5-(4-isopropylphenyl)-2-oxo-1,3,4-thiadiazol-3(2H)-yl]benzoate (0.21 g, 75%). MS (ES+): m/e 355.

Sources & evidence

ORD record
ord-9f38d826bfbf40deaa4d107dc25c22f1
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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