Benzenesulfonyl chloride → HCID 10841614, compound

HRID 1003214Notes

Reaction equation

HRID 1003214 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:19]=3[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:4][CH3:5])[CH3:2].[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C.O1CCCC1>O>[C:35]1([S:41]([N:16]2[CH2:17][CH2:18][C:19]3[C:10]4[C:11]([S:13][C:14]=3[CH2:15]2)=[N:12][C:7]([CH2:6][N:3]([CH2:1][CH3:2])[CH2:4][CH3:5])=[C:8]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:9]=4[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10505011HCID 10505011, compound

Product 1

HCID 10841614HCID 10841614, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound obtained in Example 5A (0.96 g), benzenesulfonyl chloride (0.43 g), triethylamine (0.42 ml) and tetrahydrofuran (20 ml) was stirred at room temperature for 14 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane-methanol (20:20:1, v/v) to yield ethyl 7-benzenesulfonyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (0.96 g, 76%), which was then recrystallized from ethyl acetate-hexane to yield colorless needle crystals having a melting point of 161 to 162° C. ##STR49##

Workup

  1. extractionextracted 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. washeluted with ethyl acetate-hexane-methanol (20:20:1

Sources & evidence

ORD record
ord-f37dc0e8bf3a469fa63740c3dae882a9
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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