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

HRID 2249591Notes

Reaction equation

HRID 2249591 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. MS (ISP): 272.2 (MH+).

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-17edaf1ab8a74d97913c3cc0803c4a50
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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