Sodium Hydroxide → tert-Butyl 3-thioureidopropylcarbamate

HRID 708489Notes

Reaction equation

HRID 708489 reaction equation
C([NH:9][C:10](=[S:23])[NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[C:18]([O:17][C:16](=[O:22])[NH:15][CH2:14][CH2:13][CH2:12][NH:11][C:10]([NH2:9])=[S:23])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14280415tert-Butyl 3-(3-benzoylthioureido)propylcarbamate

Product 1

HCID 20616909tert-Butyl 3-thioureidopropylcarbamateYield 145.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (3-(3-benzoylthioureido)propyl)carbamate (0.83 g, 2.45 mmol) in MeOH (15 mL) was added sodium hydroxide aqueous solution (1.96 mL, 2.45 mmol). After stirring at rt for 2 h, the reaction mixture was concentrated in vacuo and azeotropped with toluene. The crude residue was purified via silica gel chromatography (MeOH-DCM, 9% with 1% NH4OH), affording the title compound (0.83 g, 43%). LCMS: Rt=0.47 min, m/z=234.2 (M+1) Method 2m_acidic.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 9% with 1% NH4OH)

Sources & evidence

ORD record
ord-d48ed9f551354e9c8b2f61319ab58ef4
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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