Sulfuryl chloride → Amidosulfuron

HRID 1873060

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HRID 1873060 반응식
[S:1](Cl)(Cl)(=[O:3])=[O:2].[O-:6][C:7]#[N:8].[Na+].[CH3:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[NH2:16][C:17]1[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[N:18]=1>O.C(#N)C>[CH3:15][S:12]([N:11]([S:1]([NH:8][C:7]([NH:16][C:17]1[N:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[N:22]=1)=[O:6])(=[O:3])=[O:2])[CH3:10])(=[O:14])=[O:13]

참가 물질

7

반응물 4

HCID 24648Sulfuryl chlorideHCID 97632N-MethylmethanesulfonamideHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 517096Sodium Cyanate

생성물 1

HCID 91777Amidosulfuron수율 82.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
20 °C

실험 절차

340 g (2.52 mol ) of sulfuryl chloride are introduced into 1.5 l of acetonitrile, and 260 g (4.0 mol) of sodium cyanate are added in portions within the space of 20 min while stirring vigorously (20° C.). The mixture is stirred for a further 15 min and then 222 g (2.0 mol) of N-methylmethanesulfonamide are added dropwise at 25° C., the temperature is raised slowly and the mixture is heated to reflux for 200 min while stirring vigorously. Subsequently, the excess sulfuryl chloride is distilled off with the solvent under 100 mbar up to an internal temperature of 50° C. After releasing the pressure under nitrogen, 1.5 l of acetonitrile (optionally also toluene etc.) are added and 155 g (1.0 mol) of 2-amino-4,6-dimethoxy-pyrimidine are introduced at 0° C. After 75 min, 1.0 l of water is added and the precipitate is separated off and washed. 304 g of 1-[(N-methylsulfonyl-N-methyl-amino)-sulfonyl]-3-(4,6-dimethoxy-2-pyrimidyl)-urea are obtained with a melting point of 176 to 178° C. The product is in accordance with a comparison sample and, according to analysis by high pressure liquid chromatography (HPLC), has a purity of 96%; yield: 77% of theory.

후처리

  1. additionare added in portions within the space of 20 min
  2. stirringThe mixture is stirred for a further 15 min
  3. temperaturethe temperature is raised slowly
  4. temperaturethe mixture is heated
  5. temperatureto reflux for 200 min
  6. stirringwhile stirring vigorously
  7. distillationSubsequently, the excess sulfuryl chloride is distilled off with the solvent under 100 mbar up to an internal temperature of 50° C
  8. addition1.5 l of acetonitrile (optionally also toluene etc.) are added
  9. customthe precipitate is separated off
  10. washwashed

출처 및 근거

ORD 기록
ord-388dff9871744025933a7a26f291589b
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06111102

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