1,1-Dimethoxyethyl(dimethyl)amine → (E)-1-(dimethylamino)ethylidenethiourea

HRID 1893885Notes

Reaction equation

HRID 1893885 reaction equation
CO[C:3](OC)([N:5]([CH3:7])[CH3:6])[CH3:4].[NH2:10][C:11]([NH2:13])=[S:12]>C(Cl)Cl>[NH2:10][C:11](/[N:13]=[C:3](/[N:5]([CH3:7])[CH3:6])\[CH3:4])=[S:12]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 2723790Thiourea

Product 1

HCID 10654343(E)-1-(dimethylamino)ethylidenethioureaYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethyl acetamide dimethyl acetal (75 g, 0.56 mole) was added to a suspension of thiourea (33.0 g, 0.43 mole) in methylene chloride. The mixture was heated under reflux for 4 h. The solvent was removed and the residue was crystallized from 5% MeOH and diethyl ether affording (1E)-N′-(aminocarbonothioyl)-N,N-dimethylethanimidamide (47.8 g, 76% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 h
  3. customThe solvent was removed
  4. customthe residue was crystallized from 5% MeOH and diethyl ether

Sources & evidence

ORD record
ord-e1d6d386fe2f4cb59de7edebe43b520a
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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