Ethyl isothiocyanatoformate → HCID 44368998, compound

HRID 543140Notes

Reaction equation

HRID 543140 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].[CH2:30]([O:32][C:33]([N:35]=[C:36]=[S:37])=[O:34])[CH3:31]>C(Cl)(Cl)Cl>[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:36]([NH:35][C:33]([O:32][CH2:30][CH3:31])=[O:34])=[S:37])=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 13663190HCID 13663190, compound

Product 1

HCID 44368998HCID 44368998, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of 2-(2-aminoethoxymethyl)-4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (4.43 g) in dry chloroform (50 ml) was added, dropwise, a solution of ethoxycarbonylisothiocyanate (1.31 g) in dry chloroform (25 ml). The reaction was stirred for 18 hours at room temperature before evaporating the solvent and triturating the residue with ether to afford a solid which was recrystallised from diisopropyl ether to give the title compound, yield 2.6 g, m.pt. 144°.

Workup

  1. additionwas added
  2. custombefore evaporating the solvent
  3. customtriturating the residue with ether
  4. customto afford a solid which
  5. customwas recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-8607df3d42714f87bf2903e753ec19b5
Source dataset
uspto-grants-1987_04
Patent number
US04661485

Reaction notes

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