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

HRID 237081Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14]N(C2C=CC(Cl)=CC=2C)CN(C2C=CC(Cl)=CC=2C)[CH2:10]1.ClC(OC(Cl)(Cl)Cl)=[O:33].[CH:39]([NH:42][C:43]([NH:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[S:44])([CH3:41])[CH3:40].[OH-].[Na+]>>[C:46]([N:45]=[C:43]1[N:42]([CH:39]([CH3:41])[CH3:40])[C:14](=[O:33])[N:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[CH3:1])[CH2:10][S:44]1)([CH3:47])([CH3:49])[CH3:48]

Participants

Reactant 4

HCID 10426Diphosgene

HCID 14798Sodium Hydroxide

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

HCID 706005531,3,5-Tris(2-methyl-4-chlorophenyl)-hexahydro-s-triazine

Product 1

HCID 128743882-t-Butylimino-3-isopropyl-5-(2-methyl-4-chlorophenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 20.2%

Procedure

In a similar manner, 3.3 g (0.007 mole) of 1,3,5-tris(2-methyl-4-chlorophenyl)-hexahydro-s-triazine, 2.0 g (0.01 mole) of trichloromethyl chloroformate, 3.2 g (0.018 mole) of 1-isopropyl-3-t-butylthiourea, and 18 g of a 10% aqueous sodium hydroxide solution were used to obtain 0.5 g (7% yield) of 2-t-butylimino-3-isopropyl-5-(2-methyl-4-chlorophenyl)-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 387) of the formula, ##STR178## as white crystals melting at 122°-123° C.

Sources & evidence

ORD record: ord-948043ce02b940f98ee6494e279da6d5
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159328

Reaction notes

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