Diphosgene → 2-Isopropylimino-3-isopropyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

HRID 237078Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16]N(C3C=CC(OC(C)C)=CC=3)CN(C3C=CC(OC(C)C)=CC=3)[CH2:12]2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].ClC(OC(Cl)(Cl)Cl)=[O:39].[CH:45]([NH:48][C:49]([NH:51][CH:52]([CH3:54])[CH3:53])=[S:50])([CH3:47])[CH3:46].[OH-].[Na+]>>[CH:45]([N:48]=[C:49]1[N:51]([CH:52]([CH3:54])[CH3:53])[C:16](=[O:39])[N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[CH:10][CH:9]=2)[CH2:12][S:50]1)([CH3:47])[CH3:46]

Participants

Reactant 4

HCID 10426Diphosgene

HCID 14798Sodium Hydroxide

HCID 2758386Diisopropylthiourea

HCID 706005141,3,5-Tris(p-isopropoxyphenyl)-hexahydro-s-triazine

Product 1

HCID 213146952-Isopropylimino-3-isopropyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 66.8%

Procedure

In a similar manner, 2.8 g (0.006 mole) of 1,3,5-tris(p-isopropoxyphenyl)-hexahydro-s-triazine, 1.8 g (0.009 mole) of trichloromethyl chloroformate, 2.6 g (0.016 mole) of 1,3-diisopropylthiourea, and 15 g of a 10% aqueous sodium hydroxide solution were used to obtain 1.4 g (24% yield) of 2-isopropylimino-3-isopropyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 372) of the formula, ##STR172## as white crystals melting at 60°-61° C.

Sources & evidence

ORD record: ord-cf1b13d7b74f4fb98ed6fcbce499bf09
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159328

Reaction notes

Loading…