2-Aminobenzonitrile → 4-amino-1H-2lambda6,1,3-benzothiadiazine-2,2-dione

HRID 44360

반응식

HRID 44360 반응식
[C:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1N)#[N:2].[S:10]([NH2:14])([NH2:13])(=[O:12])=[O:11].C1CCN2C(=NCCC2)CC1>O>[NH:13]1[C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[C:1]([NH2:2])=[N:14][S:10]1(=[O:12])=[O:11]

참가 물질

5

반응물 3

HCID 729132-AminobenzonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82267Sulfamide

생성물 1

HCID 133303354-amino-1H-2lambda6,1,3-benzothiadiazine-2,2-dione

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

A stirred mixture of 2-cyanoaniline (236 mg, 2.0 mmol), sulfamide (192 mg, 2.0 mmol) and DBU (304 mg, 2.0 mmol) was heated at 160° C. under nitrogen for 3 days. After cooling to room temperature, the reaction mixture was diluted with water and extracted three times with EtOAc. The aqueous layer was removed under vacuum and the residue was purified by chromatography on silica gel eluting with 10% MeOH in dichloromethane to give the title compound as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ7.03 (dd, J=0.8, 8.0 Hz, 1H), 7.12 (dt, J=0.8, 8.0 Hz, 1H), 7.56 (dt, J=0.8, 8.0 Hz, 1H), 7.85 (dd, J=0.8, 8.0 Hz, 1H). MS 198 (MH+).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted three times with EtOAc
  3. customThe aqueous layer was removed under vacuum
  4. customthe residue was purified by chromatography on silica gel eluting with 10% MeOH in dichloromethane

출처 및 근거

ORD 기록
ord-f3956f9df4894fbd961f191eec64819d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541421B2

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