Formaldehyde → 2-(3-Ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

HRID 9155Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].C=O.CN.[CH3:21][N:22]1[CH2:27]COC[CH2:23]1>CCO.O>[CH2:1]([N:3]1[CH2:23][N:22]([CH3:27])[CH2:21][N:6]([C:7]2[S:8][C:9]3[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:10]=3[N:11]=2)[C:4]1=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of N-ethyl-N′-(7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)urea (10.0 g, 41.79 mmol) in EtOH/H2O (1/1, 300 mL) were added formaldehyde (37 wt % in H2O, 20.4 g, 417.87 mmol), methylamine (40 wt % in H2O, 10.8 mL, 125.37 mmol) and N-methylmorpholine (11.8 mL, 83.6 mmol). The suspension was heated to about 60° C. for about 5 hrs, then a solution had been formed. The reaction mixture was pumped down in vacuo to give 12.41 g (quantitative yield) pure product.

Workup

customa solution had been formed

Sources & evidence

ORD record: ord-18fdaa5a2062445dbc2788aa4294d857
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

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