Water → 3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

HRID 587135

Reaktionsgleichung

Reaktionsgleichung von HRID 587135
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([CH2:16][S:17]([NH2:20])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=1.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:11]=[C:12]([CH2:16][S:17]([NH2:20])(=[O:18])=[O:19])[CH:13]=[CH:14][CH:15]=2)[N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 178102,4-Dichloro-1,3,5-triazineHCID 516892Sodium BicarbonateHCID 13266255(3-Aminophenyl)methanesulfonamide

Produkt 1

HCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2,4-dichloro-1,3,5-triazine (1.0 eq) in dry DMF (0.7 M) at 0° C. under N2 atmosphere was added a solution of (3-aminophenyl)-methanesulfonamide (1.0 eq) in dry DMF (0.7 M). The reaction mixture was stirred for 2.5 h at 0° C. Then water was added and the aqueous solution was neutralized with sat. aq. NaHCO3 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4. Evaporation of solvent gave A1 as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, d6-DMSO, 300K) δ 4.26 (s, 2H), 6.89 (s, 2H), 7.15 (d, J=7.4 Hz, 1H), 7.36 (d, J=7.4 Hz, 1H), 7.66 (d, J=7.4 Hz, 1H), 8.64 (s, 1H), 9.75 (br. s, 1H), 10.83 (s, 1H). MS (ES) C10H10ClN5O2S requires: 299. found: 300 (M+H)+.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-4c537d3662694d899423edc50d09fd9b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226929B2

Verknüpfte Notizen

Wird geladen…