Acetylthiourea → HCID 22282502, compound

HRID 1062661Notes

Reaction equation

HRID 1062661 reaction equation
Br[CH:2]([C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=1)=O)[C:3]([O:5][CH3:6])=[O:4].[C:17]([NH:20][C:21]([NH2:23])=[S:22])(=[O:19])[CH3:18]>O1CCCC1>[C:17]([NH:20][C:21]1[S:22][C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=2)[N:23]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 2723593AcetylthioureaHCID 22282466HCID 22282466, compound

Product 1

HCID 22282502HCID 22282502, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (1.25 g, 4.4 mmol) in 20 mL of tetrahydrofuran was added 1-acetylthiourea (0.52 g, 4.4 mmol). The resulting mixture was stirred at 65° C. for 3 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with 10% aq HCl, saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with hexanes/ethyl acetate left the title compound as a white solid (0.4 g, 30%). MS (ESI) 302.2 (M+H)+.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. washwashed with 10% aq HCl, saturated aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a solid

Sources & evidence

ORD record
ord-314fe02a73b74a39935da5a5bae52473
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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