3-Methoxybenzylamine → 1,3-Di(3-Methoxybenzyl) Thiourea

HRID 1356604

Reaction equation

HRID 1356604 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]=[C:8]=[S:9].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][NH2:19].COC1C=C(C=CC=1)CNC(N)=S>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][NH:7][C:8]([NH:19][CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([O:14][CH3:13])[CH:16]=1)=[S:9]

Participants

5

Reactant 3

HCID 211563-MethoxybenzylamineHCID 1265123-Methoxybenzyl isothiocyanateHCID 27595411-(3-Methoxybenzyl)-2-thiourea

Product 1

HCID 102678421,3-Di(3-Methoxybenzyl) Thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

The reaction of 3-methoxybenzyl isothiocyanate with 3-methoxybenzyl amine in ethanol was repeated doubling the reaction volume and reactants and heating for 2 h at 40° C. Crystallization at −10° C., followed by evaporation of the supernatant to 20 ml and a second crystallization gave 98.4% of the theoretical yield for the two crystallizations combined. Calculated elemental analysis of 3-methoxybenzyl thiourea: C, 64.53; H, 6.37; N, 8.85; S, 10.13. Found: C, 64.30; H, 6.46; N, 8.85; S, 10.09.

Workup

  1. customCrystallization at −10° C.
  2. customfollowed by evaporation of the supernatant to 20 ml
  3. customa second crystallization
  4. customgave 98.4% of the
  5. customtheoretical yield for the two crystallizations

Sources & evidence

ORD record
ord-036573dc5ccd4663ab14d12cee8fb8be
Source dataset
uspto-grants-2003_07
Patent number
US06586628B2

Linked notes

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