N,N-Dimethylaniline → HCID 12834068, compound

HRID 851592Notes

Reaction equation

HRID 851592 reaction equation
Cl.[Cl:2][C:3]([Cl:20])([Cl:19])[CH2:4][O:5][C:6]([C:8]1[N:13]2[C:14](=[O:17])[CH:15]([NH2:16])[C@H:12]2[S:11][CH:10]([CH3:18])[CH:9]=1)=[O:7].CN(C)C1C=CC=CC=1.[S:30]([CH:34]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:35](O)=[O:36])([OH:33])(=[O:32])=[O:31].C(OOC(=O)O)C>ClCCl.C(N(CC)CC)C>[CH3:18][CH:10]1[CH:9]=[C:8]([C:6]([O:5][CH2:4][C:3]([Cl:2])([Cl:19])[Cl:20])=[O:7])[N:13]2[C:14](=[O:17])[CH:15]([NH:16][C:35](=[O:36])[CH:34]([S:30]([OH:33])(=[O:31])=[O:32])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@H:12]2[S:11]1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 413605alpha-Sulfophenylacetic acidHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochlorideHCID 21930676HCID 21930676, compound

Product 1

HCID 12834068HCID 12834068, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent2×

Procedure

A suspension of 2,2,2-trichloroethyl-2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (6.9 g) in dried dichloromethane (70 ml) was homogenized by adding triethylamine (1.48 g) and N,N-dimethylaniline (0.44 g) under stirring and ice-cooling and by stirring for 30 minutes at room temperature. A solution of triethylamine salt of mixed anhydride of 2-sulfo-2-phenylacetic acid with ethoxycarbonic acid (8.5 g) in dried dichloromethane (60 ml) was dropwise added over about 30 minutes under stirring and cooling at -20° to -25° C. to the above-mentioned solution, and the mixture was stirred for 1.5 hours at -10° to -15° C. and for 1 hour at room temperature. After the reaction, dichloromethane was removed at low temperature, and the residue was dissolved in ethyl acetate, after which the solution was washed with cooled 5% hydrochloric acid and three times with water, and then dried. The solvent was distilled off at low temperature to give 2,2,2-trichloroethyl 2-methyl-7-(2-sulfo-2-phenylacetamido)-3-cephem-4-carboxylate (11.5 g), amorphous.

Workup

  1. stirringunder stirring
  2. temperatureice-cooling
  3. stirringby stirring for 30 minutes at room temperature
  4. stirringunder stirring
  5. temperaturecooling at -20° to -25° C. to the above-mentioned solution
  6. stirringthe mixture was stirred for 1.5 hours at -10° to -15° C. and for 1 hour at room temperature
  7. customwas removed at low temperature
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washafter which the solution was washed
  10. temperaturewith cooled 5% hydrochloric acid and three times with water
  11. customdried
  12. distillationThe solvent was distilled off at low temperature

Sources & evidence

ORD record
ord-96bc49ea2e5e447ab37aae180876b4cd
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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