Dimethylformamide → 1-(2',6'-Dimethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one methanesulfonate

HRID 1262699ノート

反応式

HRID 1262699 の反応式
CN(C)C=O.S([O:11][CH3:12])(OC)(=O)=O.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[NH:21][C:22]([NH:24][C:25](=[NH:28])[NH:26][CH3:27])=O.C(N(CC)CC)C.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38]>C(#N)C>[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[N:21]1[CH:22]=[N:24][C:25]([NH:26][CH3:27])=[N:28][C:12]1=[O:11]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 6395Methanesulfonic AcidHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 178485164HCID 178485164、化合物

生成物 1

HCID 204573291-(2',6'-Dimethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one methanesulfonate収率 93%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
10 °C

実験手順

To 29.2 grams (0.4 mole) of N,N-dimethylformamide, heated to 50°-60° C., are added dropwise 50.5 grams (0.4 mole) of dimethyl sulfate while maintaining the temperature between 50° and 60° C. After the addition, the reaction mixture is heated at 70°-80° C. for four hours. The reaction mixture is diluted with acetonitrile (150 milliliters) and cooled to approximately 10° C. in an ice water bath. Then 44.0 grams (0.2 mole) of 1-(2',6'-dimethylphenyl)-3-methylamidinourea are added on one portion followed by the dropwise addition of 80.8 grams (0.8 mole) of triethylamine while keeping the temperature below 25° C. The reaction mixture is allowed to come to ambient temperature and stirred for one hour. The solvent is removed in vacuo and the residue diluted with water and the pH adjusted to 10 with ten percent (10%) aqueous sodium hydroxide. The aqueous layer is extracted with chloroform (3 times with 200 milliliters each time) and the combined extracts dried (MgSO4) and concentrated in vacuo. The residual solid is taken up in boiling acetonitrile (350 milliliters) and concentrated to approximately two-thirds of its volume on a steam bath. The hot solution is treated with 21.0 grams (0.22 mole) of methanesulfonic acid and on cooling a white crystalline solid deposits, which is filtered, washed with cold acetonitrile and vacuum dried at 80° C. for one hour to yield 60.6 grams (93%) of 1-(2',6'-dimethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one methanesulfonate, m.p. 264°-266° C. dec.

後処理

  1. temperaturewhile maintaining the temperature between 50° and 60° C
  2. additionAfter the addition
  3. temperaturethe reaction mixture is heated at 70°-80° C. for four hours
  4. customthe temperature below 25° C
  5. customto come to ambient temperature
  6. customThe solvent is removed in vacuo
  7. additionthe residue diluted with water
  8. extractionThe aqueous layer is extracted with chloroform (3 times with 200 milliliters each time)
  9. dry with materialthe combined extracts dried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. concentrationconcentrated to approximately two-thirds of its volume on a steam bath
  12. temperatureon cooling a white crystalline solid deposits, which
  13. filtrationis filtered
  14. washwashed with cold acetonitrile and vacuum
  15. customdried at 80° C. for one hour

出典と根拠

ORDレコード
ord-2631aec75b2e459e91ac941aced8b332
出典データセット
uspto-grants-1984_06
特許番号
US04452980

反応ノート

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