Pyridine → HCID 10535422, compound

HRID 1192951Notes

Reaction equation

HRID 1192951 reaction equation
[Cl-].Cl[C:3]1[NH:4]S[SH+:6][C:7]=1Cl.[CH3:9][O:10][C:11](=[O:16])/[CH:12]=[C:13](\[NH2:15])/[CH3:14].N1C=CC=CC=1>ClCCl>[C:3]([C:7]1[S:6][N:15]=[C:13]([CH3:14])[C:12]=1[C:11]([O:10][CH3:9])=[O:16])#[N:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 643918Methyl 3-aminocrotonateHCID 57361639HCID 57361639, compound

Product 1

HCID 10535422HCID 10535422, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,5-Dichloro-[1,2,3]-dithiazol-1-ylium chloride (prepared according to Chem. Ber. (1985) 118, 1632) (8.34 g, 40 mmol) was dissolved in dichloromethane (30 ml) and methyl-3-aminocrotonate (4.6 g, 40 mmol) was added dropwise at room temperature. After stirring the solution for 1 hour at room temperature pyridine (6.47 ml, 80 mmol) was added slowly. The mixture was concentrated and purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product as an orange solid (1.14 g, 15.6% yield). 1H-NMR (400 MHz, CDCl3): 2.88 (3H, s, Me), 4.0 (3H, s, Me).

Workup

  1. additionwas added slowly
  2. concentrationThe mixture was concentrated
  3. custompurified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8c1b3e34fedd4eacb9861520d0705283
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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