Mecloqualone → 3-(2-Chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one

HRID 897045

반응식

HRID 897045 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH3:19].CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:19]=[CH:22][N:23]([CH3:25])[CH3:24]

참가 물질

4

반응물 2

HCID 9567MecloqualoneHCID 78373Dimethylformamide dimethyl acetal2회

생성물 1

HCID 536897693-(2-Chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one수율 62.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

A mixture of 3-(2-chloro-phenyl)-2-methyl-3,4-dihydro-quinazolin-4-one (1.0 g, 3.69 mmol) and dimethylformamide dimethyl acetal (0.64 mL, 4.8 mmol) in dimethylformamide (4 mL) was heated to 140° C. for 24 hours. Additional dimethylformamide dimethyl acetal (0.32 mL, 2.4 mmol) was added and heating was continued for an additional 24 hours. The reaction was cooled to ambient temperature and concentrated at reduced pressure (60° C. bath temperature). The dark residue was triturated with methanol and the pale orange solid which formed was collected and dried to give 0.75 g (62%) of 3-(2-chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one which had: mp 228-230° C.; 1H 1H NMR δ 8.19 (d, J=8 Hz, 1 H), 7.91 (d, J=12.3 Hz, 1 H), 7.71-7.18 (m, 7 H), 4.10 (d, J=12.3 Hz, 1 H), 2.81 (br s, 6 H). Analysis calculated for C18H16ClN3O: C, 66.36; H, 4.95; N, 12.90. Found: C, 66.20; H, 5.03; N, 12.79.

후처리

  1. temperatureheating
  2. temperatureThe reaction was cooled to ambient temperature
  3. concentrationconcentrated at reduced pressure (60° C. bath temperature)
  4. customThe dark residue was triturated with methanol
  5. customthe pale orange solid which formed
  6. customwas collected
  7. customdried

출처 및 근거

ORD 기록
ord-9ec17971598e4b4e8f829fb8df34cf1d
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921764B2

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