Hydrazinecarboxylic acid, ethyl ester → 1,2,3-Thiadiazole, 4,5-bis(4-methoxyphenyl)-

HRID 2372358Notes

Reaction equation

HRID 2372358 reaction equation
[C:1]1([C:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=2)=O)[CH:8]=[CH:7][C:4]([O:5][CH3:6])=[CH:3][CH:2]=1.C(OC(=O)[NH:24][NH2:25])C.O=[S:28](Cl)Cl>>[CH3:6][O:5][C:4]1[CH:7]=[CH:8][C:1]([C:9]2[N:25]=[N:24][S:28][C:11]=2[C:12]2[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=2)=[CH:2][CH:3]=1

Participants

4

Reactant 3

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 24386Thionyl ChlorideHCID 67120Desoxyanisoin

Product 1

HCID 105181841,2,3-Thiadiazole, 4,5-bis(4-methoxyphenyl)-

Conditions

Temperature
60 °C

Procedure

The hydrazone (7.0 g, 20 mmol) derived from desoxyanisoin (Aldrich) and ethylcarbazate was added to 20 ml of SOCl2 ;which had been cooled in an ice bath. The reaction was heated at 60° C. for 1 hour, cooled and then the solvent was removed under vacuum. The crude residue was triturated with ether affording 7.5 g of crude material, m.p. 80°-82° C. This was recrystallized from ether affording 3.59 g (60%) of 7, m.p. 84°-86° C. as red crystals. A simple column filtration through silica afforded white, analytically pure crystals of 7, m.p. 84°-86° C.

Workup

  1. temperaturehad been cooled in an ice bath
  2. temperaturecooled
  3. customthe solvent was removed under vacuum
  4. customThe crude residue was triturated with ether affording 7.5 g of crude material, m.p. 80°-82° C
  5. customThis was recrystallized from ether affording 3.59 g (60%) of 7, m.p. 84°-86° C. as red crystals
  6. filtrationA simple column filtration through silica afforded white

Sources & evidence

ORD record
ord-755a9a65cbda40818ab551a00566c105
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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