Diphosgene → 2-t-Butylimino-3-s-butyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

HRID 237079Notes

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:49][C:50]([NH:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[S:51])([CH2:47][CH3:48])[CH3:46].[OH-].[Na+]>>[C:53]([N:52]=[C:50]1[N:49]([CH:45]([CH2:47][CH3:48])[CH3:46])[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:51]1)([CH3:54])([CH3:56])[CH3:55]

Participants

Reactant 4

HCID 10426Diphosgene

HCID 14798Sodium Hydroxide

HCID 129062961-s-Butyl-3-t-butylthiourea

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

Product 1

HCID 213147682-t-Butylimino-3-s-butyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 66.2%

Procedure

Similarly, 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, 3.0 g (0.016 mole) of 1-s-butyl-3-t-butylthiourea, and 15 g of a 10% aqueous sodium hydroxide solution were used to obtain 1.5 g (25% yield) of 2-t-butylimino-3-s-butyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 374)of the formula, ##STR173## as colorless oily substance (nD20 1.5402).

Sources & evidence

ORD record: ord-d780b915abe6401eab82913522f71a3f
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159328

Reaction notes

Loading…