Triethylamine → HCID 178469321, compound

HRID 280572Notes

Reaction equation

HRID 280572 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[NH:7][C:8]([CH3:29])=[C:9]([C:25]([O:27][CH3:28])=[O:26])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[Cl:24])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].S(O)(O)(=O)=O.CS[C:37](=[NH:39])[NH2:38].C(N(CC)CC)C>C(O)CC>[Cl:24][C:18]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH:10]1[C:9]([C:25]([O:27][CH3:28])=[O:26])=[C:8]([CH3:29])[NH:7][C:6]([CH2:5][O:4][CH2:3][CH2:2][NH:1][C:37]([NH2:39])=[NH:38])=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752702-Methyl-2-thiopseudourea sulfateHCID 13663190HCID 13663190, compound

Product 1

HCID 178469321HCID 178469321, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

2-(2-Aminoethoxymethyl)-4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (5.0 g) and S-methylisothiourea sulphate (3.45 g) was suspended in n-propanol (120 ml) and triethylamine (30 ml) and refluxed for 17 hours. After evaporation to dryness, the residual oil was partitioned between aqueous sodium bicarbonate and methylene chloride. The organic layer was dried (MgSO4), filtered and evaporated. The resultant beige solid was triturated with hexane to give the title compound (4.1 g), N.M.R. (CDCl3, 60 MHz): 3H 1.15(t), 3H 3.55(s), 4H 3.7(m), 2H 4.0(q), 2H 4.7(s), 1H 5.45(s), 8H 7.25(m).

Workup

  1. customAfter evaporation to dryness
  2. customthe residual oil was partitioned between aqueous sodium bicarbonate and methylene chloride
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resultant beige solid was triturated with hexane

Sources & evidence

ORD record
ord-fdf3322d8ae74823bac84c0aba9411c5
Source dataset
uspto-grants-1986_05
Patent number
US04590195

Reaction notes

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