Aniline → HCID 70590409, compound

HRID 1395501Notes

Reaction equation

HRID 1395501 reaction equation
Br[C:2]1([CH3:29])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4][CH2:3]1.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.F[B-](F)(F)F.[Ag+]>[NH:30]([CH2:3][C:2]1([CH3:29])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:13])[Cl:14])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 70361012HCID 70361012, compound

Product 1

HCID 70590409HCID 70590409, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trichloroethyl 3-bromo-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate (1.10 g) was dissolved in methylene chloride (15 ml) and to this solution was added aniline (0.28 g). And to the solution was added silver fluoroborate (0.5 g) under stirring under ice-cooling and the mixture was stirred for 4 hours at the same temperature. After the reaction was completed, the reaction mixture was filtered. The filtrate was washed with a dilute aqueour solution of phosphoric acid and then with water, dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography on silica gel (25 g) and eluted with chloroform. The eluate was separated into fractions of each about 20 ml and the second to eighth fractions were collected and then the solvent was distilled off to give 2,2,2-trichloroethyl 2-anilinomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.54 g), mp 148° to 149° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 4 hours at the same temperature
  3. filtrationthe reaction mixture was filtered
  4. washThe filtrate was washed with a dilute aqueour solution of phosphoric acid
  5. dry with materialwith water, dried over magnesium sulfate
  6. concentrationconcentrated
  7. washeluted with chloroform
  8. customThe eluate was separated into fractions of each about 20 ml
  9. customthe second to eighth fractions were collected
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-af22cd1042674857847b695d37c6a7dd
Source dataset
uspto-grants-1980_05
Patent number
US04203897

Reaction notes

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