Diphosgene → 5-{2-[(Phenylmethyl)thio]phenyl}-1,3,4-oxadiazol-2(3H)-one

HRID 34873Notes

Reaction equation

HRID 34873 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[C:9]1([CH2:15][S:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([NH:21][NH2:22])=[O:20])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCOCC1>[C:9]1([CH2:15][S:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]2[O:20][C:2](=[O:3])[NH:22][N:21]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 142088052-(Benzylsulfanyl)benzohydrazide

Product 1

HCID 139588535-{2-[(Phenylmethyl)thio]phenyl}-1,3,4-oxadiazol-2(3H)-oneYield 79.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution containing 12.2 g of trichloromethyl chloroformate in 130 ml of p-dioxane was added portionwise 16 g of 2-[(phenylmethyl)thio]benzoic acid, hydrazide [prepared by the procedure of South African Patent Application No. 838,416 (1983)] to cause a slight exotherm to 37° C. After stirring at ambient temperature for 0.5 hr., the suspension was refluxed for 6 hours, then cooled to 25° C. and poured onto excess ice/water to yield a precipitate. The mixture was filtered, washed with water and the isolated solid was recrystallized from acetonitrile to yield 14 g of the subject compound: m.p. 169°-172° C.

Workup

  1. customprepared by the procedure of South African Patent Application No
  2. customto 37° C
  3. temperature, the suspension was refluxed for 6 hours
  4. temperaturecooled to 25° C.
  5. customto yield a precipitate
  6. filtrationThe mixture was filtered
  7. washwashed with water
  8. customthe isolated solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4664c9396b2a4a6ea9726df8d45d1fc4
Source dataset
uspto-grants-1988_08
Patent number
US04764205

Reaction notes

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