N,N-Dimethylaniline → HCID 12833985, compound

HRID 1660597Notes

Reaction equation

HRID 1660597 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.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[CH2:42][C:43](Cl)=[O:44]>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:43](=[O:44])[CH2:42][C:38]3[S:37][CH:41]=[CH:40][CH:39]=3)[C@H:5]2[S:4]1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 12833985HCID 12833985, compoundYield 86.8%

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 solution was dropwise added a solution of (2-thienyl)acetyl chloride (2.0 g) in dried dichloromethane (10 ml) under stirring and cooling at the same temperature, 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, the residue was dissolved in ether, allowed to stand, after which the precipitated crystals were collected by filtration and dried to give crystals of 2,2,2-trichloroethyl 2-methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylate (3.2 g), mp 161° to 162° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-b543efc7f26d45488ac5ed1e926b675a
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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