Chlorosuccinimide → HCID 57826544, compound

HRID 1845691Notes

Reaction equation

HRID 1845691 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=2)=[CH:5][N:4]=[N:3]1.C1C(=O)N([Cl:23])C(=O)C1>CN(C)C=O.CCOC(C)=O>[Cl:23][C:5]1[N:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 57826849HCID 57826849, compound

Product 1

HCID 57826544HCID 57826544, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thiophenecarboxylate (500 mg, 2.24 mmol) and NCS (1196 mg, 8.96 mmol) in N,N-Dimethylformamide (DMF) (10 ml) was heated at 50° C. for 2 hr. The reaction mixture was diluted with 50 ml of EtOAc. The organic layer was washed with H2O (50 ml×2) and brine (50 ml), and then concentrated to give 460 mg of a crude mixture, which was used in next step without further separation. LCMS (ES) m/z 258.0 (M+H)+.

Workup

  1. washThe organic layer was washed with H2O (50 ml×2) and brine (50 ml)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5a548a0ceff54c08bd71dd751d92c240
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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