2-Butanone, 3-bromo- → HCID 86597775, compound

HRID 1716539Notes

Reaction equation

HRID 1716539 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][NH:10][C:11]([NH2:13])=[S:12])([CH3:4])([CH3:3])[CH3:2].Br[CH:16]([CH3:20])[C:17](=O)[CH3:18].CCN(C(C)C)C(C)C>C(O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[S:12][C:16]([CH3:20])=[C:17]([CH3:18])[N:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 131422-Butanone, 3-bromo-HCID 81531DiisopropylethylamineHCID 22726781HCID 22726781, compound

Product 1

HCID 86597775HCID 86597775, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2-thioureido-ethyl)-carbamic acid tert-butyl ester [CAS 331779-96-5] (3.6 g), 3-bromo-2-butanone (2.45 g), and DIPEA (5.5 ml) in ethanol (100 ml) was stirred overnight at RT and refluxed 1 hour. The mixture was concentrated. Ethyl acetate was added. Insoluble parts were filtered off and the remaining solution was extracted with brine. The organic layer was dried, evaporated and purified by flash chromatography yielding after crystallization 0.86 g of white crystals.

Workup

  1. temperaturerefluxed 1 hour
  2. concentrationThe mixture was concentrated
  3. additionEthyl acetate was added
  4. filtrationInsoluble parts were filtered off
  5. extractionthe remaining solution was extracted with brine
  6. customThe organic layer was dried
  7. customevaporated
  8. custompurified by flash chromatography
  9. customyielding
  10. customafter crystallization 0.86 g of white crystals

Sources & evidence

ORD record
ord-6c0334fe7c4a4effbe145ea5a7fe4260
Source dataset
uspto-grants-2010_09
Patent number
US07803819B2

Reaction notes

Loading…