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

HRID 711629노트

반응식

HRID 711629 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

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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) δ 7.03 (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-f97924ee76fe4d0a874c52b815f8e5ba
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181276B2

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