2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 70581734, compound

HRID 2052180Notes

Reaction equation

HRID 2052180 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:44](=[O:45])[N:12]2[C:13]([C:28]([O:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])=[C:14]([CH:17]=[N:18][NH:19][C:20](=[S:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][S:16][C@H:11]12)=[O:8].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:44](=[O:45])[N:12]2[C:13]([C:28]([O:30][CH:31]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:29])=[C:14]([C:17]3[S:27][C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:19][N:18]=3)[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 131711679HCID 131711679, compound

Product 1

HCID 70581734HCID 70581734, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1 g of benzhydryl 7-thienylacetamido-3-thiobenzoylhydrazonomethyl-3-cephem-4-carboxylate in 10 ml of dioxane is added 0.28 g of DDQ, followed by stirring at room temperature for 30 minutes. The reaction mixture is filtered and the filtrate cake is washed with a small amount of dioxane. The combined filtrate is evaporated to dryness in vacuo and the residue recrystallized from ethyl acetate to give 0.6 g of benzhydryl 7-thienylacetamido-3-(5-phenyl-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate as pale yellow crystals.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filtrate cake is washed with a small amount of dioxane
  3. customThe combined filtrate is evaporated to dryness in vacuo
  4. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cefd25b33531494380f4ce57960650fd
Source dataset
uspto-grants-1980_01
Patent number
US04182866

Reaction notes

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