Formaldehyde → HCID 20346835, compound

HRID 1701508Notes

Reaction equation

HRID 1701508 reaction equation
C=O.[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([NH2:14])=[S:13].CN.[CH3:17][N:18]([CH3:21])[CH:19]=O>C(OCC)C>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N:11]1[CH2:19][N:18]([CH3:21])[CH2:17][NH:14][C:12]1=[S:13]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 6329MethylamineHCID 2798617Thiourea, (2,4-dimethylphenyl)- (9CI)

Product 1

HCID 20346835HCID 20346835, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Formaldehyde (4.86 g, 37% solution, 30 mmole) was added to a solution of 2,4-dimethyl-phenyl thiourea (4.5 g, 24 mmole) in dimethylformamide (40 ml) and the solution was stirred for 15 minutes at room temperature. Methylamine (3.72 g, 30 mmole) was added dropwise with stirring and the mixture was heated under reflux at 100° C. for 4 hours. The solution was cooled and the solvent removed under vacuum to yield an oil. This was diluted with diethyl-ether and refrigerated to yield 1-(2,4-dimethylphenyl)-5-methyl-tetrahydro-s-triazin-2[1H]-thione as a white crystalline solid which was collected, washed with a little cold diethyl ether and dried (4.5 g, 77%), m.p. 140°-143° C.

Workup

  1. stirringwith stirring
  2. temperaturethe mixture was heated
  3. temperatureunder reflux at 100° C. for 4 hours
  4. temperatureThe solution was cooled
  5. customthe solvent removed under vacuum
  6. customto yield an oil

Sources & evidence

ORD record
ord-df899ce7f7f54392bb8428e7736ac98c
Source dataset
uspto-grants-1980_03
Patent number
US04193994

Reaction notes

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