N-chlorosuccinamide → HCID 86669542, compound

HRID 524405Notes

Reaction equation

HRID 524405 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]([C:8]1[N:9]=[C:10]([NH2:13])[S:11][CH:12]=1)([CH3:7])[CH3:6])[CH3:2].[Cl:15]NC(=O)CCC(N)=O>C(#N)C>[CH2:1]([O:3][C:4](=[O:14])[C:5]([C:8]1[N:9]=[C:10]([NH2:13])[S:11][C:12]=1[Cl:15])([CH3:7])[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 15238416N-chlorosuccinamideHCID 8366865176687-08-6

Product 1

HCID 86669542HCID 86669542, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-(2-Amino-thiazol-4-yl)-2-methyl-propionic acid ethyl ester (0.3 g, 1.40 mmol) was taken in 10 mL of acetonitrile and N-Chlorosuccinamide (0.224 g, 1.68 mmol) was added the reaction was stirred for 1 hr. at room temperature. After completion of reaction acetonitrile was evaporated under reduced pressure and the residue was partitioned between water (25 mL) and ethyl acetate (25 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layer was washed with brine and dried over anhydrous sodium sulphate and the solvent was removed in vacuo. The residue was purified by preparative TLC plate (mobile phase 40% ethyl acetate in hexane) to afford pure compound (0.3 g).

Workup

  1. customat room temperature
  2. customwas evaporated under reduced pressure
  3. customthe residue was partitioned between water (25 mL) and ethyl acetate (25 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×25 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified by preparative TLC plate (mobile phase 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-718b0b7b56904ee99f0657950fe86525
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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