Ethyl isothiocyanatoformate → Ethyl({[6-(3-thienyl)pyridin-2-yl]amino}carbonothioyl)carbamate

HRID 2382761Notes

Reaction equation

HRID 2382761 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[C:10]([NH2:12])[CH:9]=[CH:8][CH:7]=2)=[CH:2]1.[CH2:13]([O:15][C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH3:14]>O1CCOCC1>[CH2:13]([O:15][C:16](=[O:17])[NH:18][C:19]([NH:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[N:11]=1)=[S:20])[CH3:14]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 457880412-Amino-6-(3-thienyl)pyridine

Product 1

HCID 59437441Ethyl({[6-(3-thienyl)pyridin-2-yl]amino}carbonothioyl)carbamateYield 73.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-(3-thienyl)pyridin-2-amine (3.70 g; 21.0 mmol; 1.0 eq.) and ethoxycarbonyl isothiocyanate (2.73 mL; 24.1 mmol; 1.15 eq.) in dioxane (100 mL) was stirred at rt overnight. The precipitate formed was filtered and washed with c-Hex to give the title compound as a white solid (4.73 g; 73%). HPLC, Rt: 4.26 min. (purity 99.9%). LC/MS, M+(ESI): 308.3.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with c-Hex

Sources & evidence

ORD record
ord-da970898fe1e468482b2cbe2251a905e
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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