Chlorosuccinimide → HCID 66645284, compound

HRID 2199228Notes

Reaction equation

HRID 2199228 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([C:10]1[S:14][C:13]([Br:15])=[N:12][CH:11]=1)[CH2:8]C)([CH3:4])([CH3:3])[CH3:2].[Cl:17]N1C(=O)CCC1=O>C(#N)C>[C:1]([O:5][C:6](=[O:16])[N:7]([C:10]1[S:14][C:13]([Br:15])=[N:12][C:11]=1[Cl:17])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 66645331HCID 66645331, compound

Product 1

HCID 66645284HCID 66645284, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2-bromo-thiazol-5-yl)-ethyl-carbamic acid tert-butyl ester (4.0 g, 13 mmol) in acetonitrile (75 mL) was added N-chlorosuccinimide (3.48 g, 26 mmol) in one portion and the reaction mixture was stirred for 16 h. The reaction mixture was concentrated and the crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give the desired product as a grey solid (4.2 g, 95%): IR (KBr) 1738 cm−1; 1H NMR (300 MHz, CDCl3) δ 3.61 (q, J=7.1 Hz, 2H), 1.43 (s, 9H), 1.16 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-becb01393c8c4149939826b2384ddac4
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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