N,N-Dimethylaniline → HCID 12775083, compound

HRID 434993Notes

Reaction equation

HRID 434993 reaction equation
CN(C1C=CC=CC=1)C.C[Si](C)(C)Cl.C1(CC([NH:24][CH:25]2[C:46](=[O:47])[N:27]3[C:28]([C:43]([OH:45])=[O:44])=[C:29]([O:32][S:33]([C:36]4[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=4)(=[O:35])=[O:34])[CH2:30][S:31][C@H:26]23)=O)C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl.O.CO.C(N(CC)CC)C>[NH2:24][CH:25]1[C:46](=[O:47])[N:27]2[C:28]([C:43]([OH:45])=[O:44])=[C:29]([O:32][S:33]([C:36]3[CH:37]=[CH:38][C:39]([CH3:40])=[CH:41][CH:42]=3)(=[O:34])=[O:35])[CH2:30][S:31][C@H:26]12

Participants

9

Reactant 4

HCID 949N,N-DimethylanilineHCID 6397ChlorotrimethylsilaneHCID 24819Phosphorus pentachlorideHCID 88608153HCID 88608153, compound

Product 1

HCID 12775083HCID 12775083, compoundYield 44.1%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (3.41 g.), N,N-dimethylphenylamine (10.3 g.) and trimethylchlorosilan (5.64 g.) were added to a stirred solution of 7-phenylacetamido-3-tosyloxy-3-cephem-4-carboxylic acid (15 g.) in methylene chloride (150 ml.) at room temperature in turn, and the solution was stirred at room temperature for an hour. Phosphorus pentachloride (7.03 g.) was added to the solution at -35° C. and stirred at -25° to -20° C. for 1.5 hours. Methanol (61 ml.) was added to the solution and stirred at the same temperature for 40 minutes. To the resultant solution was added water (50 ml.) at -20° to -10° C. The organic layer was separated and washed with water twice. The aqueous layer and the washings were combined, and washed with methylene chloride twice and diethyl ether in turn. After the solution was adjusted to pH 4.7 with 10% aqueous sodium hydroxide under cooling, the precipitates were collected by filtration, washed with water, acetone and diethyl ether in turn, and then dried over phosphorus pentoxide to give 7-amino-3-tosyloxy-3-cephem-4-carboxylic acid (5.01 g.), mp 172° C. (dec.).

Workup

  1. stirringstirred at -25° to -20° C. for 1.5 hours
  2. stirringstirred at the same temperature for 40 minutes
  3. customThe organic layer was separated
  4. washwashed with water twice
  5. washwashed with methylene chloride twice
  6. temperatureunder cooling
  7. filtrationthe precipitates were collected by filtration
  8. washwashed with water, acetone and diethyl ether in turn
  9. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-85ad9453d4e84287af298621be16b1e3
Source dataset
uspto-grants-1983_08
Patent number
US04399133

Reaction notes

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