N,N-Dimethylaniline → HCID 70582645, compound

HRID 2052174Notes

Reaction equation

HRID 2052174 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.S1C=CC=C1CC([NH:15][CH:16]1[C:34](=[O:35])[N:18]2[C:19]([C:31]([OH:33])=[O:32])=[C:20]([C:23]3[S:24][C:25]([N:28]([CH3:30])[CH3:29])=[N:26][N:27]=3)[CH2:21][S:22][C@H:17]12)=O.CN(C)C1C=CC=CC=1.C[Si](C)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl.O.CO.N1C=CC=CC=1>[NH2:15][CH:16]1[C:34](=[O:35])[N:18]2[C:19]([C:31]([OH:33])=[O:32])=[C:20]([C:23]3[S:24][C:25]([N:28]([CH3:30])[CH3:29])=[N:26][N:27]=3)[CH2:21][S:22][C@H:17]12

Participants

10

Reactant 5

HCID 949N,N-DimethylanilineHCID 6398DichlorodimethylsilaneHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 70581518HCID 70581518, compound

Product 1

HCID 70582645HCID 70582645, compoundYield 45.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a suspension of 0.625 g of powdered phosphorous pentachloride in 20 ml of dichloromethane is added 0.474 g of pyridine under stirring at -40° C. To the resulting mixture is added dropwise a solution of 0.422 g of 7-thienylacetamido-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylic acid (obtained in Example 42) in 10 ml of dichloromethane, 0.242 g of dimethylaniline and then 0.3 ml of dimethyldichlorosilane under stirring at -40° C. After stirring for 30 minutes at 0° C., to the reaction mixture is added 5 ml of methanol under stirring at -40° C., and the mixture is poured into cold water. The aqueous layer is neutralized to pH 5.5 with an aqueous solution of sodium bicarbonate and washed three times with dichloromethane. The solution is charged on a column of Amberlite XAD-II and eluted with water. The fractions containing the desired product are collected and lyophilized to give 0.140 g of 7-amino-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylic acid.

Workup

  1. stirringAfter stirring for 30 minutes at 0° C., to the reaction mixture
  2. stirringunder stirring at -40° C.
  3. washwashed three times with dichloromethane
  4. additionThe solution is charged on a column of Amberlite XAD-II
  5. washeluted with water
  6. additionThe fractions containing the desired product
  7. customare collected

Sources & evidence

ORD record
ord-c2178830604a47dd91b6563af3de1c57
Source dataset
uspto-grants-1980_01
Patent number
US04182866

Reaction notes

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