Aniline → HCID 70590409, compound

HRID 1438784Notes

Reaction equation

HRID 1438784 reaction equation
Br[CH2:2][C:3]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]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]([CH2:2][C:3]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]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 70590409HCID 70590409, compound

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (1.10 g) dissolved in methylene chloride (15 ml). To this solution was added aniline (0.28 g) under cooling at -10° C and then silver fluoroborate (0.-3 g), after which the mixture was stirred for 2 hours. After the reaction was completed, the reaction mixture was washed with a dilute phosphoric acid aqueous solution and then with water, dried over magnesium sulfate, after which the solvent was distilled off. The residue was subjected to column chromatography at silica gel (20 g) and eluted with chloroform. The eluate was separated into fractions of each about 20 ml. The second to seventh fractions were collected and the solvent was distilled off to give 2,2,2-trichloroethyl 2-anilinomethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate (0.8- g), mp 148° to 149° C.

Workup

  1. washthe reaction mixture was washed with a dilute phosphoric acid aqueous solution
  2. dry with materialwith water, dried over magnesium sulfate
  3. distillationafter which the solvent was distilled off
  4. washeluted with chloroform
  5. customThe eluate was separated into fractions of each about 20 ml
  6. customThe second to seventh fractions were collected
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5c31e973fb4045308ae63a8b9d10a8cb
Source dataset
uspto-grants-1977_11
Patent number
US04056521

Reaction notes

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