Tert-Butylamine → 4-t-Butylamino-2-chloro-6-nitroquinazoline

HRID 1250601

반응식

HRID 1250601 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O.C(N(C(C)C)C=O)(C)C.[C:30]([NH2:34])([CH3:33])([CH3:32])[CH3:31]>O>[C:30]([NH:34][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[C:9]([Cl:18])[N:8]=1)([CH3:33])([CH3:32])[CH3:31]

참가 물질

6

반응물 4

HCID 6385Tert-ButylamineHCID 24813Phosphorus oxychlorideHCID 75912N,N-bis(1-methylethyl)formamideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

생성물 1

HCID 183265064-t-Butylamino-2-chloro-6-nitroquinazoline수율 64.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 250 mg (1.21 mmol) of 6-nitroquinazoline-2,4(1H,3H)-dione were added 5.00 ml (53.64 mmol) of phosphorus oxychloride and 0.18 ml (1.21 mmol) of diisopropylformamide, and the resulting mixture was subjected to heating under reflux for 24 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 5 ml of acetonitrile, followed by addition of 1.26 ml (12.10 mmol) of t-butylamine under ice cooling and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 218 mg (64.2%) of the title compound.

후처리

  1. temperatureto heating
  2. temperatureunder reflux for 24 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 5 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by a silica gel column

출처 및 근거

ORD 기록
ord-27d5da839434492eacac3aa1683bc395
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339089B2

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