Hydrochloric Acid → HCID 15462640, compound

HRID 1003212Notes

Reaction equation

HRID 1003212 reaction equation
C([N:9]1[CH2:14][CH2:13][C:12]2[C:15]3[C:16]([S:39][C:11]=2[CH2:10]1)=[N:17][C:18]([CH2:33][N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])=[C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:20]=3[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=O)C1C=CC=CC=1.Cl.[OH-].[Na+]>O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:18]([CH2:33][N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])[N:17]=[C:16]3[S:39][C:11]4[CH2:10][NH:9][CH2:14][CH2:13][C:12]=4[C:15]=23)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15462639HCID 15462639, compound

Product 1

HCID 15462640HCID 15462640, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the compound obtained in Example 4A (2.09 g) and concentrated hydrochloric acid (8 ml)-water (16 ml) was stirred at 90° C. for 4 hours. After the reaction mixture was alkalinized with 1N NaOH, it was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residual solid was recrystallized from ethyl acetate-hexane to yield ethyl 4-(4-chlorophenyl)-2-(N,N-diethylaminomethyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (1.34 g, 79%) as colorless needle crystals having a melting point of 104 to 106° C. ##STR46##

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. customThe residual solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9f37d716d829440f8de75855fd7762d0
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

Loading…