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

HRID 237077Notes

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:42][C:43]([NH:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[S:44])([CH3:41])[CH3:40].[OH-].[Na+]>>[CH:39]([N:42]=[C:43]1[N:45]([CH2:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[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:44]1)([CH3:41])[CH3:40]

Participants

Reactant 4

HCID 10426Diphosgene

HCID 14798Sodium Hydroxide

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

HCID 12725928N-Benzyl-N'-propan-2-ylthiourea

Product 1

HCID 213147102-Isopropylimino-3-benzyl-5-(p-methoxyphenyl)tetrahydro-1,3,5-thiadiazin-4-oneYield 155.8%

Procedure

Similarly, 1.4 g (0.0033 mole) of 1,3,5-tris(p-methoxyphenyl)-hexahydro-s-triazine, 1 g (0.005 mole) of trichloromethyl chloroformate, 2.1 g (0.01 mole) of 1-isopropyl-3-benzylthiourea, and 9 ml of a 10% sodium hydroxide solution were used to obtain 1.9 g (52% yield) of 2-isopropylimino-3-benzyl-5-(p-methoxyphenyl)tetrahydro-1,3,5-thiadiazin-4-one (compound No. 356) of the formula, ##STR157## as white crystals melting at 114° C.

Sources & evidence

ORD record: ord-e0512e2674554e698bbf89c058329084
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159328

Reaction notes

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