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

HRID 237080Notes

Reaction equation

HRID 237080 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].[CH2:45]([NH:52][C:53]([NH:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[S:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[OH-].[Na+]>>[CH2:45]([N:52]=[C:53]1[N:55]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[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:54]1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

5

Reactant 4

HCID 10426DiphosgeneHCID 14798Sodium HydroxideHCID 838375N,N'-DibenzylthioureaHCID 706005141,3,5-Tris(p-isopropoxyphenyl)-hexahydro-s-triazine

Product 1

HCID 213146972-Benzylimino-3-benzyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 84.2%

Procedure

Similarly, 2.0 g (0.004 mole) of 1,3,5-tris(p-isopropoxyphenyl)-hexahydro-s-triazine, 1.2 g (0.006 mole) of trichloromethyl chloroformate, 3.1 g (0.012 mole) of 1,3-dibenzylthiourea, and 11 g of a 10% aqueous sodium hydroxide solution were used to obtain 1.5 g (28% yield) of 2-benzylimino-3-benzyl-5-(p-isopropoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 375) of the formula, ##STR174## as white crystals melting at 141°-142° C.

Sources & evidence

ORD record
ord-ce8e6a83b93f4deba16e51b56953d8b1
Source dataset
uspto-grants-1979_06
Patent number
US04159328

Reaction notes

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