Lithium Hydroxide → N-[1-ethyl-1-(hydroxymethyl)propyl]thiourea

HRID 1436372Notes

Reaction equation

HRID 1436372 reaction equation
[CH2:1]([C:3]([NH:8][C:9]([NH:11]C(=O)C1C=CC=CC=1)=[S:10])([CH2:6][OH:7])[CH2:4][CH3:5])[CH3:2].[Li+].[OH-]>O1CCCC1.CO.O>[CH2:1]([C:3]([NH:8][C:9]([NH2:11])=[S:10])([CH2:6][OH:7])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86618579N-({[1-ethyl-1-(hydroxymethyl)propyl]amino}carbonothioyl)benzamide

Product 1

HCID 86618580N-[1-ethyl-1-(hydroxymethyl)propyl]thioureaYield 68%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-({[1-ethyl-1-(hydroxymethyl)propyl]amino}carbonothioyl)benzamide (6.8779 g, 24.5 mmol), prepared in the previous step, and 1 M LiOH (29.4 mL, 29.4 mmol) in 200 mL of tetrahydrofuran plus 200 mL of methanol plus 100 mL of water was stirred under nitrogen at room temperature for 21 h. The reaction was concentrated under reduced pressure to remove most of the tetrahydrofuran and methanol. The solid present was collected by filtration and dried under reduced pressure to give N-[1-ethyl-1-(hydroxymethyl)propyl]thiourea (2.9228 g, 68%) as a white solid, mp 148-151° C.; MS (ESI) m/z 177 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove most of the tetrahydrofuran and methanol
  3. filtrationThe solid present was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ca4ac7044e2848b785f5b5a0ecfc690e
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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