Carbon Dioxide → N-(2,6-Diethyl-phenyl)-N'-tert.-butyl-thiourea

HRID 1701561Notes

Reaction equation

HRID 1701561 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[N:11]=[C:12]=[S:13])[CH3:2].C([C:16]1C=CC=[C:19](CC)[C:17]=1[NH2:18])C.[C:25](=O)([O-])[O-].[Ca+2].C(Cl)(Cl)=S.C(=O)=O>C(Cl)Cl.O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([NH:18][C:17]([CH3:19])([CH3:25])[CH3:16])=[S:13])[CH3:2]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 113692,6-DiethylanilineHCID 1411932,6-Diethylphenyl isothiocyanate

Product 1

HCID 20346927N-(2,6-Diethyl-phenyl)-N'-tert.-butyl-thiourea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2,6-Diethyl-phenyl isothiocyanate can be prepared as follows: 100 g of 2,6-diethylaniline in 200 ml of methylene chloride are added dropwise at 0°-5°, whilst stirring, to a mixture of 500 ml of methylene chloride, 300 ml of water, 120 g of calcium carbonate and 92 g of thiophosgene. The mixture is then heated to the reflux temperature until the evolution of CO2 has ended. The cooled batch is filtered and the methylene chloride layer is separated off, dried with calcium chloride and fractionated.

Workup

  1. filtrationThe cooled batch is filtered
  2. customthe methylene chloride layer is separated off
  3. dry with materialdried with calcium chloride

Sources & evidence

ORD record
ord-f9f97215daf94e67ae5df4197d44dfa3
Source dataset
uspto-grants-1980_03
Patent number
US04194008

Reaction notes

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