Water → N-(2-Aminoethyl)-N'(3,5-dimethoxyphenyl)thiourea

HRID 1193523

Reaction equation

HRID 1193523 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]=[C:12]=[S:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:14]([NH2:17])[CH2:15][NH2:16].O>CCOCC>[NH2:16][CH2:15][CH2:14][NH:17][C:12]([NH:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[S:13]

Participants

5

Reactant 3

HCID 962WaterHCID 3301EthylenediamineHCID 1454223,5-Dimethoxyphenyl isothiocyanate

Product 1

HCID 13604911N-(2-Aminoethyl)-N'(3,5-dimethoxyphenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

A slurry of 9.75 g (0.05 mole) of 3,5-dimethoxyphenyl isothiocyanate in 27 ml of ether was added dropwise to a stirred solution of 3.0 g (0.05 mole) of ethylenediamine at room temperature. A five-degree rise in temperature was noted at the start of the one hour addition period. A solid appeared during the addition, and stirring was continued for 2.5 hours. The batch was allowed to stand overnight, and 100 ml of H2O was added. The solid was removed by filtration and the filtrate acidified with 4.5 ml of concentrated HCl and evaporated to dryness on the steam bath. The residue was sonicated with 100 ml of water and warmed to 50° C. for 10 minutes. This was filtered and basified to pH 10 with 10% NaOH. This gave 2.6 g of 14, m.p. 125°-126° C. Analysis satisfactory for C11H17N3O2S.

Workup

  1. additionA five-degree rise in temperature was noted at the start of the one hour addition period
  2. additionA solid appeared during the addition
  3. waitto stand overnight
  4. customThe solid was removed by filtration
  5. customevaporated to dryness on the steam bath
  6. customThe residue was sonicated with 100 ml of water
  7. filtrationThis was filtered

Sources & evidence

ORD record
ord-55c9c6c8b341407bb24a3bb2999b6d79
Source dataset
uspto-grants-1989_03
Patent number
US04810725

Linked notes

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