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

HRID 587135

반응식

HRID 587135 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-4c537d3662694d899423edc50d09fd9b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226929B2

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