N,N-Dimethylaniline → HCID 131711252, compound

HRID 851587

Reaction equation

HRID 851587 reaction equation
Cl.[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH2:19])[C@H:5]2[S:4]1.C(N(CC)CC)C.CN(C)C1C=CC=CC=1.[C:37]1([CH2:43][C:44](Cl)=[S:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:14])[Cl:15])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH:19][C:44](=[S:45])[CH2:43][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:5]2[S:4]1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8471TriethylamineHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochlorideHCID 19906501Benzylthiocarbonyl chloride

Product 1

HCID 131711252HCID 131711252, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

2,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (3.0 g) was suspended in dried dichloromethane (50 ml) and then dissolved by adding triethylamine (0.72 g) and dimethylaniline (1.9 g) under cooling at -15° C. To a mixture was dropwise added a solution of phenylthioacetyl chloride (2.2 g) in dried dichloromethane (10 ml) under stirring, and the mixture was stirred for 1.5 hours at the same temperature. After the reaction, the reaction mixture was in turn washed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water and then dried. After the solvent was distilled off, ether was added to the residue, after which the precipitated crystals were collected by filtration and dried to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylate (3.4 g), mp 140° to 142° C.

Workup

  1. dissolutiondissolved
  2. stirringthe mixture was stirred for 1.5 hours at the same temperature
  3. customAfter the reaction
  4. washwashed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water
  5. customdried
  6. distillationAfter the solvent was distilled off
  7. additionether was added to the residue
  8. filtrationafter which the precipitated crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-dcc77b214b0f4656adb3610d244174a5
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Linked notes

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