Sodium Hydroxide → HCID 178418894, compound

HRID 10733Notes

Reaction equation

HRID 10733 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[C:5]([NH:7][NH:8][C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[S:10])=O.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[C:5]1[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([SH:10])=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22084281-[(2,4-Dimethoxybenzoyl)amino]-3-(2-methylpropyl)thiourea

Product 1

HCID 178418894HCID 178418894, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ex-109C: A solution of 1-(2,4-dimethoxy-benzoyl)amino-3-isobutyl-thiourea (Ex-109B, 0.5 g, 1.61 mmol) and sodium hydroxide (0.999M, 4.8 mL, 4.8 mmol) in ethanol (30 mL) was refluxed for one day. The solvent was removed under reduced pressure and the residue redissolved in ethyl acetate. The solution of ethyl acetate was washed with water and brine, dried over sodium sulfate, and concentrated to give 5-(2,4-dimethoxy-phenyl)-4-isobutyl-4H-[1,2,4]triazole-3-thiol (0.1 g). Additional product (0.36 g, 98% overall) was obtained by extracting the water wash with dichloromethane and a mixture of isopropyl alcohol (33%, v/v, in dichloromethane). 1H NMR (CDCl3) δ 10.82 (bs, 1H), 7.24 (d, J=8.1 Hz, 1H), 6.56 (dd, J=8.1, 2.4 Hz, 1H), 6.51 (d, J=2.4 Hz, 1H), 3.85 (s, 3H), 3.77 (s, 3H), 3.72 (d, J=6.7 Hz, 2H), 2.17–2.08 (m, 1H), 0.70 (d, J=6.7 Hz, 6H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue redissolved in ethyl acetate
  3. washThe solution of ethyl acetate was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0fa6753b39494df987413a4807ef9f7e
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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