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

HRID 237076Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14]N(C3C=CC(OC)=CC=3)CN(C3C=CC(OC)=CC=3)[CH2:10]2)=[CH:5][CH:4]=1.ClC(OC(Cl)(Cl)Cl)=[O:33].[CH:39]([NH:43][C:44]([NH:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[S:45])([CH2:41][CH3:42])[CH3:40].[OH-].[Na+]>>[C:47]([N:46]=[C:44]1[N:43]([CH:39]([CH2:41][CH3:42])[CH3:40])[C:14](=[O:33])[N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][S:45]1)([CH3:48])([CH3:50])[CH3:49]

Participants

Reactant 4

HCID 10426Diphosgene

HCID 14798Sodium Hydroxide

HCID 110585791,3,5-Triazine, hexahydro-1,3,5-tris(4-methoxyphenyl)-

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

Product 1

HCID 128744022-t-Butylimino-3-s-butyl-5-(p-methoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-oneYield 76.9%

Procedure

Similarly, 2.7 g (0.0067 mole) of 1,3,5-tris(p-methoxyphenyl)-hexahydro-s-triazine, 2.0 g (0.01 mole) of trichloromethyl chloroformate, 3.8 g (0.02 mole) of 1-s-butyl-3-t-butylthiourea, and 16 ml of a 10% sodium hydroxide solution were used to obtain 1.8 g (26% yield) of 2-t-butylimino-3-s-butyl-5-(p-methoxyphenyl)-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 355) of the formula: ##STR156## as white crystals melting at 63° C.

Sources & evidence

ORD record: ord-d728dafd5aa347c0bfea81c7e2039390
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159328

Reaction notes

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