Methyl Isocyanate → 2-(Methylcarbamoyl)amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

HRID 1938545노트

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HRID 1938545 반응식
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[N:15]=[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:27])[CH:12]=2)[N:7]=1>CS(C)=O>[CH3:1][NH:2][C:3]([NH:5][C:6]1[N:15]=[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:27])[CH:12]=2)[N:7]=1)=[O:4]

참가 물질

4

반응물 2

HCID 12228Methyl IsocyanateHCID 211839282-Amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

생성물 1

HCID 211840132-(Methylcarbamoyl)amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline수율 12.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
50 °C

실험 절차

4 ml of dimethyl sulfoxide and 260 mg of methyl isocyanate were added to 500 mg of 2-amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. The obtained mixture was stirred at 50° C. for 3 hours and distilled under a reduced pressure to remove excess methyl isocyanate, followed by the addition of chloroform and water. The mixture thus obtained was filtered and the filtrate was extracted with chloroform twice. The organic layers were combined, washed with water twice, dried over magnesium sulfate and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (benzene/acetone) and recrystallized (from benzene/chloroform/ethanol) to give 72 mg of the title compound.

후처리

  1. distillationdistilled under a reduced pressure
  2. customto remove excess methyl isocyanate
  3. additionfollowed by the addition of chloroform and water
  4. customThe mixture thus obtained
  5. filtrationwas filtered
  6. extractionthe filtrate was extracted with chloroform twice
  7. washwashed with water twice
  8. dry with materialdried over magnesium sulfate
  9. distillationdistilled under a reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography (benzene/acetone)
  12. customrecrystallized (from benzene/chloroform/ethanol)

출처 및 근거

ORD 기록
ord-4b12d53166dd4e7d99731a1617e522ae
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05693652

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