Aniline → HCID 70590547, compound

HRID 2083166Notes

Reaction equation

HRID 2083166 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1([CH3:36])[CH:14]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])[N:13]2[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:12]2[S:11][CH2:10]1>C(Cl)Cl.[B-](F)(F)(F)F.[Ag+]>[NH:1]([C:9]1([CH3:36])[CH:14]([C:15]([O:17][CH2:18][C:19]([Cl:20])([Cl:21])[Cl:22])=[O:16])[N:13]2[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:12]2[S:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 70361012HCID 70361012, compound

Product 1

HCID 70590547HCID 70590547, compound

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolvent

Procedure

Aniline (0.28 g) was added to a solution of 2,2,2-trichloroethyl 3-bromo-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate (1.10 g) in methylene chloride (15 ml). To the solution was added silver fluoborate 0.45 g under ice-cooling under stirring and stirred at the same temperature for 4 hours. After the reaction, the mixture was filtered and the filtrate was washed with dilute phosphoric acid aqueous solution and water in turn. The solution was dried over magnesium sulphate and concentrated. The residue was subjected to column chromatography on silica gel (25 g) using chloroform. The 12th to 13th fractions of fractions, each of which was separated into 20 cc, were concentrated to give oily 2,2,2-trichloroethyl 3-anilino-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate.

Workup

  1. temperaturecooling
  2. stirringstirred at the same temperature for 4 hours
  3. customAfter the reaction
  4. filtrationthe mixture was filtered
  5. washthe filtrate was washed with dilute phosphoric acid aqueous solution and water in turn
  6. dry with materialThe solution was dried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe 12th to 13th fractions of fractions, each of which was separated into 20 cc
  9. concentrationwere concentrated

Sources & evidence

ORD record
ord-28669d2ab5f24154a6d6a69749011f1a
Source dataset
uspto-grants-1978_04
Patent number
US04084049

Reaction notes

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