Diphosgene → 2-t-Butylimino-3-isopropyl-5-(2,6-dimethylphenyl)tetrahydro-1,3,5-thiadiazin-4-one

HRID 237083Notes

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.[CH:19]([NH:22][C:23]([NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[S:24])([CH3:21])[CH3:20].[OH-].[Na+]>>[C:26]([N:25]=[C:23]1[N:22]([CH:19]([CH3:21])[CH3:20])[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:24]1)([CH3:29])([CH3:28])[CH3:27]

Participants

Reactant 4

HCID 10426Diphosgene

HCID 14798Sodium Hydroxide

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

HCID 12750667N-tert-Butyl-N'-propan-2-ylthiourea

Product 1

HCID 213147662-t-Butylimino-3-isopropyl-5-(2,6-dimethylphenyl)tetrahydro-1,3,5-thiadiazin-4-oneYield 9%

Procedure

Similarly, 2.7 g (0.02 mole) of N-methylene-2,6-dimethylaniline, 2.0 g (0.01 mole) of trichloromethyl chloroformate, 3.3 g (0.019 mole) of 1-isopropyl-3-t-butylthiourea, and 18 g of a 10% aqueous sodium hydroxide solution were used to obtain 0.3 g (7% yield) of 2-t-butylimino-3-isopropyl-5-(2,6-dimethylphenyl)tetrahydro-1,3,5-thiadiazin-4-one (compound No. 388) of the formula, ##STR180## as white crystals melting at 103°-104° C.

Sources & evidence

ORD record: ord-78ff9e70c6a341909f81d7583fa1683d
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159328

Reaction notes

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