N,N-Dimethylaniline → HCID 131714489, compound

HRID 1907028Notes

Reaction equation

HRID 1907028 reaction equation
S1C=CC=C1CC([NH:9][CH:10]1[C:28](=[O:29])[N:12]2[C:13]([C:25]([O-:27])=[O:26])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH2:15][S:16][C@H:11]12)=O.CN(C)C1C=CC=CC=1.C[Si]([Cl:43])(C)C.P(Cl)(Cl)(Cl)(Cl)Cl.C(O)CC(O)C>C(Cl)Cl>[ClH:24].[ClH:43].[NH2:9][CH:10]1[C:28](=[O:29])[N:12]2[C:13]([C:25]([O-:27])=[O:26])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH2:15][S:16][C@H:11]12

Participants

7

Reactant 5

HCID 949N,N-DimethylanilineHCID 6397ChlorotrimethylsilaneHCID 78961,3-ButanediolHCID 24819Phosphorus pentachlorideHCID 131714491HCID 131714491, compound

Product 1

HCID 131714489HCID 131714489, compoundYield 177.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a mixture of 7-(2-thienylacetamido)-3-(3-chloro-1-pyridiniomethyl)-3-cephem-4-carboxylate (22.5 g) and N,N-dimethylaniline (60.0 g) in methylene chloride (400 ml) was added dropwise trimethylsilylchloride (50.0 g) at ambient temperature under stirring, which was continued for 15 minutes at the same temperature. The reaction mixture was cooled to -30° C. and phosphorus pentachloride (31.2 g) was added thereto under stirring, which was continued for one hour at -30° to -25° C. The reaction mixture was added to a cold solution of 1,3-butanediol (45 g) in methylene chloride (400 ml) under cooling in an ice-bath and stirring, which was continued for one hour at ambient temperature. The resulting precipitate was filtered, washed with methylene chloride and redissolved in methanol (50 ml). After the solution was treated with activated charcoal (1 g), the filtrate was poured into acetone (500 ml) under stirring, which was continued for 30 minutes at ambient temperature. The resulting precipitate was filtered, washed with acetone and dried to give 7-amino-3-(3-chloro-1-pyridiniomethyl)-3-cephem-4-carboxylate dihydrochloride (17.7 g), mp. 160° to 165° C. (dec.).

Workup

  1. stirringunder stirring
  2. waitwhich was continued for one hour at -30° to -25° C
  3. temperatureunder cooling in an ice-bath
  4. stirringstirring
  5. waitwhich was continued for one hour at ambient temperature
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with methylene chloride
  8. dissolutionredissolved in methanol (50 ml)
  9. additionAfter the solution was treated with activated charcoal (1 g)
  10. additionthe filtrate was poured into acetone (500 ml)
  11. stirringunder stirring
  12. waitwhich was continued for 30 minutes at ambient temperature
  13. filtrationThe resulting precipitate was filtered
  14. washwashed with acetone
  15. customdried

Sources & evidence

ORD record
ord-8bdf4d46f27949c1b4ac7febd24eda3c
Source dataset
uspto-grants-1987_03
Patent number
US04654422

Reaction notes

Loading…