N-Iodosuccinimide → Tert-butyl(3-cyano-5-iodo-2-thienyl)carbamate

HRID 386133Notes

Reaction equation

HRID 386133 reaction equation
[I:1]N1C(=O)CCC1=O.[C:9]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])#[N:10]>ClCCl>[C:19]([O:18][C:17](=[O:23])[NH:16][C:12]1[S:13][C:14]([I:1])=[CH:15][C:11]=1[C:9]#[N:10])([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 65143119tert-Butyl (3-cyanothiophen-2-yl)carbamate

Product 1

HCID 70842571Tert-butyl(3-cyano-5-iodo-2-thienyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Iodosuccinimide (9.28 g, 41.2 mmol, 1.0 eq) was added to a stirred mixture of tert-butyl (3-cyano-2-thienyl)carbamate (9.25 g, 4.1.2 mmol, 1.0 eq) in dichloromethane (82 ml, 0.5 M) and the mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane and washed with 1N sodium hydroxide (300 mL), sodium thiosulfate (2×300 mL), water (2×300 mL), and brine. The organic layers was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as a solid.

Workup

  1. washwashed with 1N sodium hydroxide (300 mL), sodium thiosulfate (2×300 mL), water (2×300 mL), and brine
  2. dry with materialThe organic layers was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-787a1b8792d04111af2c827767fdf7c8
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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