Formaldehyde → N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-(3-pyridylmethyl)urea

HRID 9104

Reaktionsgleichung

Reaktionsgleichung von HRID 9104
[CH2:1]([N:3]1CN(C)C[N:5]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([N+]([O-])=O)[CH:16]=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:22])[CH3:2].C(NC(N[C:29]1S[C:31]2[CH:37]=C([N+]([O-])=O)C=C[C:32]=2[N:33]=1)=O)C.C=O.CN.[CH3:45][N:46]1CCOCC1>CO.CCO.O>[C:45]([C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([NH:5][C:4]([NH:3][CH2:1][C:2]3[CH:29]=[N:33][CH:32]=[CH:31][CH:37]=3)=[O:22])[S:11][C:12]=2[CH:18]=1)#[N:46]

Komponenten

8

Edukt 5

HCID 712FormaldehydeHCID 6329MethylamineHCID 79724-MethylmorpholineHCID 9813955N-Ethyl-N'-(6-nitro-1,3-benzothiazol-2-yl)ureaHCID 219855321-Ethyl-5-methyl-3-(6-nitro-1,3-benzothiazol-2-yl)-1,3,5-triazinan-2-one

Produkt 1

HCID 21985518N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-(3-pyridylmethyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

General procedure for synthesizing 1-ethyl-5-methyl-3-(6-nitro-1,3-benzothiazol-2-yl)-1,3,5-triazinan-2-one: N-Ethyl-N′-(6-nitro-1,3-benzothiazol-2-yl)urea is suspended in an alkanol/water mixture, preferably 1:1 EtOH/H2O at room temperature. A 37% aqueous solution of formaldehyde is added followed by addition of a 2M solution of MeNH2 in MeOH, then about 2 mole equivalents of N-methylmorpholine. The solution is warmed to about 70–85° C., preferably 80° C., then allowed to stir for about 4–24 hours, preferably 4 hours. The slurry is then cooled to room temperature, filtered and washed well with water, dried and the title product is isolated. General Procedure for Grignard Addition:

Aufarbeitung

  1. temperatureThe slurry is then cooled to room temperature
  2. filtrationfiltered
  3. washwashed well with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e8b7ee04ec75448d86e69b5a0568d5fc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091227B2

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