Triethylamine → HCID 70067608, compound

HRID 1073829Notes

Reaction equation

HRID 1073829 reaction equation
[CH2:1](N(CC)CC)C.[CH3:8][O:9][CH2:10][CH2:11][O:12]CCl.[C:15]([C:20]1[CH:25]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)[C:24]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:23]([CH3:40])[NH:22][C:21]=1[CH2:41][SH:42])([O:17][CH2:18][CH3:19])=[O:16]>C1COCC1.C(OCC)(=O)C.O>[C:15]([C:20]1[CH:25]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)[C:24]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:23]([CH3:40])[NH:22][C:21]=1[CH:41]([O:12][CH2:11][CH2:10][O:9][CH3:8])[S:42][CH3:1])([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 116758332-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Product 1

HCID 70067608HCID 70067608, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

0.205 ml of triethylamine (1,476 mmol.) and 0.133 ml of methoxyethoxymethylchloride (MEM-Cl) (1,476 mmol.) are added to a solution of 3,5-dicarboethoxy-6-methyl-2-mercaptomethyl-4-(m-nitrophenyl)-1,4-dihydropyridine (400 mg, 0,984 mmol.) in anhydrous THF. The mixture is left to react for 30' at room temperature under nitrogen atmosphere. The reaction mixture is diluted with a mixture of ethyl acetate-water 1:1 (100 ml) and the phases are separated: the organic phase is washed with a 5% sodium bicarbonate solution (3×20 ml) and water (2×20 ml), dried on sodium sulphate, filtered and the solvent is evaporated under reduced pressure, yielding 422 mg of 3,5-dicarboethoxy-6-methyl-2-(methoxyethoxy-methylthiomethyl)-4-(m-nitrophenyl)-1,4-dihydropyridine, as a glassy yellow oil.

Workup

  1. waitThe mixture is left
  2. customto react for 30' at room temperature under nitrogen atmosphere
  3. customthe phases are separated
  4. washthe organic phase is washed with a 5% sodium bicarbonate solution (3×20 ml) and water (2×20 ml)
  5. customdried on sodium sulphate
  6. filtrationfiltered
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-a8fd497a5ee44a1198014aa573573647
Source dataset
uspto-grants-1990_11
Patent number
US04971984

Reaction notes

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