4-Bromophenacyl bromide → HCID 59822262, compound

HRID 1670538Notes

Reaction equation

HRID 1670538 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=O)[CH2:7]Br)=[CH:4][CH:3]=1.[CH:12]1([CH2:15][NH:16][C:17]([NH2:19])=[S:18])[CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:19]=[C:17]([NH:16][CH2:15][CH:12]3[CH2:14][CH2:13]3)[S:18][CH:7]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 516892Sodium BicarbonateHCID 2795339N-Cyclopropylmethylthiourea

Product 1

HCID 59822262HCID 59822262, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Slurry 4-bromophenacyl bromide (11.2 g, 50 mmol) in absolute ethanol (50 mL). Add N-cyclopropylmethyl-thiourea (6.5 g, 50 mmol) and sodium bicarbonate (4.2 g, 50 mmol), heat to reflux for 2 h, then stir at room temperature overnight. Concentrate to ¼ volume and partition between water/EtOAc (4:1, 500 mL). Extract the aqueous layer with EtOAc (2×75 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the title compound (14.0 g, 91%) as an off-white solid that was used without further purification. MS (ES+) m/z: 310 (M+H)+.

Workup

  1. temperatureto reflux for 2 h
  2. concentrationConcentrate
  3. custompartition between water/EtOAc (4:1, 500 mL)
  4. extractionExtract the aqueous layer with EtOAc (2×75 mL)
  5. dry with materialDry the combined organic extracts over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7a818e54f2c74bdb9d0979692aa8fdcb
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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