N-(Phenylmethyl)thiourea → HCID 22282455, compound

HRID 1062669Notes

Reaction equation

HRID 1062669 reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:18]([NH:25][C:26]([NH2:28])=[S:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH2:18]([NH:25][C:26]1[S:27][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=2)[N:28]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 737375N-(Phenylmethyl)thioureaHCID 22282470HCID 22282470, compound

Product 1

HCID 22282455HCID 22282455, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (0.60 g, 2.03 mmol) in 20 mL of absolute ethanol was added N-benzylthiourea (0.34 g, 2.03 mmol). The resulting mixture was stirred at 80° 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 saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to-yield a solid. Trituration with hexanes/ethyl ether left the title compound as an off-white solid (0.36 g, 49%). MS (ESI) 364.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-29e6df5669b54eaba1676aa57785b3be
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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