Triethylamine → HCID 23320817, compound

HRID 280573Notes

Reaction equation

HRID 280573 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([CH3:23])[NH:16][C:15]([CH2:24][O:25][CH2:26][CH2:27][NH:28][CH3:29])=[C:14]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([CH3:23])[NH:16][C:15]([CH2:24][O:25][CH2:26][CH2:27][N:28]([S:2]([CH3:1])(=[O:4])=[O:3])[CH3:29])=[C:14]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13663196HCID 13663196, compound

Product 1

HCID 23320817HCID 23320817, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (0.144 g) was added to a solution of 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(methylamino)ethoxy methyl]-1,4-dihydropyridine (0.50 g) and triethylamine (0.126 g) in dichloromethane (15 ml). The mixture was stirred at room temperature for 1 hour, poured into ice-water and the layers separated. The organic layer was washed with water, dried (Na2SO4) and evaporated. Scratching the residual oil afforded a solid which was recrystallised from methanol to give the title compound (0.33 g), m.p. 93°-95° C. Found: C, 53.32; H, 5.97; N, 5.64. C22H29ClN2O7S requires C, 53.32; H, 5.92; N, 5.71%.

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customafforded a solid which
  6. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-514243c1cfc847feb594dab72a729997
Source dataset
uspto-grants-1986_05
Patent number
US04590195

Reaction notes

Loading…