Thiourea → HCID 90303417, compound

HRID 1051957Notes

Reaction equation

HRID 1051957 reaction equation
Br[CH:2]1[C:6](=O)[CH2:5][CH2:4][CH:3]1[C:8]#[N:9].[NH2:10][C:11]([NH2:13])=[S:12]>O1CCOCC1>[NH2:13][C:11]1[S:12][C:2]2[CH:3]([C:8]#[N:9])[CH2:4][CH2:5][C:6]=2[N:10]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 90303209HCID 90303209, compound

Product 1

HCID 90303417HCID 90303417, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-3-oxocyclopentanecarbonitrile (crude from A.1.2.1.; ca. 13 g) and thiourea (13.77 g, 181 mmol) in dioxane (600 mL) was stirred at 80° C. for 1 h. The mixture was allowed to cool to RT, quenched with aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. Purification by means of CC (2-20% MeOH (0.5% Et3N)/DCM) provided a brown solid.

Workup

  1. temperatureto cool to RT
  2. customquenched with aq. sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washlayers were washed with brine
  5. dry with materialdried over MgSO4
  6. customPurification by means of CC (2-20% MeOH (0.5% Et3N)/DCM)
  7. customprovided a brown solid

Sources & evidence

ORD record
ord-c2584b849e3e4aa38ddb2116771f866c
Source dataset
uspto-grants-2016_07
Patent number
US09388198B2

Reaction notes

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