Dimethylamine → HCID 20189346, compound

HRID 1789025Notes

Reaction equation

HRID 1789025 reaction equation
S(Cl)(Cl)=[O:2].[CH3:5][C:6]1[NH:11][C:10]([C:12]([O-])=O)=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:7]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30].[CH3:34][NH:35][CH3:36]>C(Cl)Cl.CN(C)C=O.C1C=CC=CC=1>[CH3:34][N:35]([CH3:36])[C:12]([C:10]1[NH:11][C:6]([CH3:5])=[C:7]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:9]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:2]

Participants

7

Reactant 3

HCID 674DimethylamineHCID 24386Thionyl Chloride2×HCID 20189396HCID 20189396, compound

Product 1

HCID 20189346HCID 20189346, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.05 ml) was added to a solution of 3,5-diethyl 1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2,3,5-pyridinetricarboxylate (0.25 g, 0.62 mmoles) in methylene chloride (10 ml) containing dimethylformamide (1 drop). After 2 hours at room temperature further thionyl chloride (0.05 ml) was added and the solution was refluxed for 30 mins. After cooling to room temperature 10% dimethylamine in benzene (1 ml) was added and the mixture stirred for 30 mins. The solvent was evaporated and the residue dissolved in dilute hydrochloric acid and ether. The organic extract was washed with brine, dried (Na2SO4) and the solvent removed in vacuo to leave the title compound (0.2 g). M+ 431; nmr (CDCl3) δ 5.12 (s,H), 3.05 (s,3H), 2.95 (s,3H).

Workup

  1. temperaturethe solution was refluxed for 30 mins
  2. additionwas added
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in dilute hydrochloric acid
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3b2c0a48c868439f90ea3bd03ef94952
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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