Diphosgene → 2-Methylimino-3-methyl-5-(2,6-dimethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

HRID 237082Notes

Reaction equation

[CH2:1]=[N:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:10].ClC([O:14][C:15](Cl)(Cl)Cl)=O.[CH3:19][NH:20][C:21]([NH:23][CH3:24])=[S:22].[OH-].[Na+]>>[CH3:19][N:20]=[C:21]1[N:23]([CH3:24])[C:15](=[O:14])[N:2]([C:3]2[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:10])[CH2:1][S:22]1

Participants

Reactant 4

HCID 10426Diphosgene

HCID 14798Sodium Hydroxide

HCID 141978Methanimine, N-(2,6-dimethylphenyl)-

HCID 2723631N,N'-Dimethylthiourea

Product 1

HCID 213147312-Methylimino-3-methyl-5-(2,6-dimethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 22.5%

Procedure

Similarly, 2.7 g (0.02 mole) of N-methylene-2,6-dimethylaniline, 2.0 g of trichloromethyl chloroformate, 2.0 g (0.02 mole) of 1,3-dimethylthiourea, and 18 g of a 10% aqueous sodium hydroxide solution were used to obtain 0.6 g (12% yield) of 2-methylimino-3-methyl-5-(2,6-dimethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 389) of the formula, ##STR179## as a colorless oily substance (nD20 1.5967).

Sources & evidence

ORD record: ord-74934cae358f41c5998d8b14ae062304
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159328

Reaction notes

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