Methyl 2-chloro-3-oxopentanoate → HCID 18672263, compound

HRID 1057767Notes

Reaction equation

HRID 1057767 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]([NH2:13])=[S:12].Cl[CH:15]([C:20](=O)[CH2:21][CH3:22])[C:16]([O:18][CH3:19])=[O:17]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[S:12][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:20]([CH2:21][CH3:22])[N:13]=1

Participants

4

Reactant 2

HCID 545096Methyl 2-chloro-3-oxopentanoateHCID 2731098N-(2,4,6-Trichlorophenyl)thiourea

Product 1

HCID 18672263HCID 18672263, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 2,4,6-trichlorophenylthiourea (scheme 1: (B)) (3.25 g, 12.72 mmoles) and methyl 2-chloro-3-oxopentanoate (Scheme 1: (C)) (1.92 mL, 1.1 equiv.) in ethanol (60 mL) was heated at reflux for 16 hours. The solvent was removed in vacuo and the product was recrystallized from methanol (4.49 g, 97%). H1 NMR (CDCl3) δ 1.15 (3H, t), 2.91 (2H, q), 3.75 (3H, s), 7.47 (2H, s), 9.10 (1H, br).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed in vacuo
  3. customthe product was recrystallized from methanol (4.49 g, 97%)

Sources & evidence

ORD record
ord-28ca9b4f932c4793a4ab38bf570d1b7e
Source dataset
uspto-grants-2003_02
Patent number
US06515005B2

Reaction notes

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