Ethyl isothiocyanatoformate → 1-(6-Bromo-4-methyl-pyridin-2-yl)-3-carboethoxy-thiourea

HRID 1472868Notes

Reaction equation

HRID 1472868 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([O:12][C:13]([N:15]=[C:16]=[S:17])=[O:14])[CH3:11]>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:16]([NH:15][C:13]([O:12][CH2:10][CH3:11])=[O:14])=[S:17])[CH:5]=[C:4]([CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 221765076-Bromo-4-methylpyridin-2-amine

Product 1

HCID 595897291-(6-Bromo-4-methyl-pyridin-2-yl)-3-carboethoxy-thiourea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-4-methyl-pyridin-2-ylamine (0.5 g, 2.67 mmol) in dichloromethane (20 ml) cooled to 5° C. was added ethoxycarbonyl isothiocyanate (0.32 ml, 2.67 mmol) dropwise over 15 min. The reaction mixture was then allowed to warm to room temperature at which it was stirred for 16 h. Evaporation in vacuo gave a solid that was collected by filtration and thoroughly washed with cyclohexane to give the desired product. Yield 0.59 g, 69%. LCMS MI: 317.92+319.94, RT: 5.05 min, Method: 2

Workup

  1. customEvaporation in vacuo
  2. customgave a solid
  3. filtrationthat was collected by filtration
  4. washthoroughly washed with cyclohexane

Sources & evidence

ORD record
ord-e9e8f1b3bf5e4a309a76ec6ea7eeaaf6
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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