Ethyl isothiocyanatoformate → Ethyl aminon-(3-bromopyridin-2-YL)methanethiocarbamate

HRID 1913090Notes

Reaction equation

HRID 1913090 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([O:11][C:12]([N:14]=[C:15]=[S:16])=[O:13])[CH3:10]>ClCCl>[CH2:9]([O:11][C:12](=[O:13])[NH:14][C:15](=[S:16])[NH:1][C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:10]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 59199107Ethyl aminon-(3-bromopyridin-2-YL)methanethiocarbamateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-3-bromopyridine (50.0 g, 289 mmol, 1 equiv) in dichloromethane (500 mL) was added dropwise ethoxycarbonyl isothiocyanate (39.0 g, 297 mmol, 1.03 equiv) at room temperature. After 2 h, dichloromethane was removed in vacuo to provide crude ethyl[(3-bromopyridin-2-yl)carbamothioyl]carbamate (88 g).

Workup

  1. customdichloromethane was removed in vacuo

Sources & evidence

ORD record
ord-3a20c74e4bd747bf808bb1e5db1e2a5a
Source dataset
uspto-grants-2013_12
Patent number
US08609687B2

Reaction notes

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