Dimethylcarbamoyl Chloride → HCID 23324637, 화합물

HRID 1380834노트

반응식

HRID 1380834 반응식
[Cl:1][CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[N:6]=[C:5]([CH3:10])[N:4]=1.[H-].[Na+].[H][H].[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[CH3:15][N:16]([CH3:20])[C:17](=[O:18])[O:9][C:7]1[N:6]=[C:5]([CH3:10])[N:4]=[C:3]([CH2:2][Cl:1])[CH:8]=1

참가 물질

6

반응물 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, 화합물HCID 178433451HCID 178433451, 화합물

생성물 1

HCID 23324637HCID 23324637, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

5 g (0.0315 mol) of 4-chloromethyl-6-hydroxy-2-methyl-pyrimidine are introduced portionwise under nitrogen into a suspension of 0.80 g (0.0331 mol) of sodium hydride (freed from a 50% dispersion in oil by two-fold extraction with n-pentane) in 50 ml of absolute tetrahydrofuran. After completion of the hydrogen evolution 2.9 ml (0.0315 mol) of dimethylcarbamoyl chloride are added dropwise and the mixture is heated at reflux for 16 hours. The cooled mixture is subsequently diluted with 150 ml of toluene, washed in succession with in each case 50 ml of 5% sodium bicarbonate solution, 0.1N hydrochloric acid and saturated sodium chloride solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residual oil is filtered briefly on silica gel with 90% diethyl ether in n-hexane. There is obtained 4-chloromethyl-2-methyl-6-pyrimidinyl N,N-dimethylcarbamate as a colourless oil, nD22 1.5265.

후처리

  1. extractionfreed from a 50% dispersion in oil by two-fold extraction with n-pentane) in 50 ml of absolute tetrahydrofuran
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 16 hours
  4. washwashed in succession with in each case 50 ml of 5% sodium bicarbonate solution, 0.1N hydrochloric acid and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe residual oil is filtered briefly on silica gel with 90% diethyl ether in n-hexane

출처 및 근거

ORD 기록
ord-14b2637f228e48ed81ddb640461e70a8
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04584295

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