Dimethylformamide → HCID 14502354, compound

HRID 1248880Notes

Reaction equation

HRID 1248880 reaction equation
Br[CH2:2][C:3]([NH:5][CH:6]1[C:28](=[O:29])[N:8]2[CH:9]=[C:10]([CH2:16][NH:17][C:18](=[O:27])[C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[CH:11](C(O)=O)[S:12][C@H:7]12)=[O:4].[C:30]1([C:36]2[O:37][C:38]([SH:41])=[N:39][N:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CN(C)C=O.[C:47](=O)([O-:49])[O-:48].[K+].[K+]>CCOCC>[C:30]1([C:36]2[O:37][C:38]([S:41][CH2:2][C:3]([NH:5][CH:6]3[C:28](=[O:29])[N:8]4[C:9]([C:47]([OH:49])=[O:48])=[C:10]([CH2:16][NH:17][C:18](=[O:27])[C:19]5[C:20]([Cl:26])=[CH:21][CH:22]=[CH:23][C:24]=5[Cl:25])[CH2:11][S:12][C@H:7]34)=[O:4])=[N:39][N:40]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 70468138HCID 70468138, compoundHCID 178527944HCID 178527944, compound

Product 1

HCID 14502354HCID 14502354, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.0 g. of 7-bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-carboxylic acid and 0.36 g. of 2-phenyl-5-mercapto-1,3,4-oxadiazole were dissolved in 10 ml. of dimethyl formamide and 0.28 g. of calcinated potassium carbonate were added. The reaction mixture was stirred at room temperature for 8 hours, 30 ml. of ether were added, the precipitate was filtered off and dissolved in 30 ml. of water. The solution was adjusted to pH 5 by adding dilute sulphuric acid and extracted with 20 ml. of ethyl acetate. The aqueous layer was adjusted to pH 2 by adding dilute sulphuric acid and extracted with 60 ml. of ethyl acetate. The organic extract was dried over magnesium sulphate. The solvent was evaporated in vacuo and the residue was treated with ether and dried. 0.72 g. of 7-(2-phenyl-1,3,4-oxadiazole-5-ylthio)acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid were obtained.

Workup

  1. filtrationthe precipitate was filtered off
  2. dissolutiondissolved in 30 ml
  3. additionby adding dilute sulphuric acid
  4. extractionextracted with 20 ml
  5. additionby adding dilute sulphuric acid
  6. extractionextracted with 60 ml
  7. extractionThe organic extract
  8. dry with materialwas dried over magnesium sulphate
  9. customThe solvent was evaporated in vacuo
  10. additionthe residue was treated with ether
  11. customdried

Sources & evidence

ORD record
ord-9b17ff1409e545dd90400b75a1299171
Source dataset
uspto-grants-1986_12
Patent number
US04626533

Reaction notes

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