Acetic Acid → 3-Amino-8-bromo-N,N,-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonamide

HRID 1377064

반응식

HRID 1377064 반응식
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[C:15]([Br:17])=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23].C(O)(=O)C.CO>O>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:18]([N:24]([CH2:25][CH3:26])[CH2:22][CH3:23])(=[O:20])=[O:19])[C:15]([Br:17])=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 887MethanolHCID 8021DiethylamineHCID 1361209353-Amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2h)-one-9-sulfonylchloride

생성물 1

HCID 1358381053-Amino-8-bromo-N,N,-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonamide수율 59%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

3-Amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonylchloride (1.10 g, 2.8 mmole) and diethylamine(5 ml) were dissolved in water(15 ml) and heated to reflux for 30 minutes. The reaction mixture was cooled to room temperature and neutralized with dilute acetic acid. The collected precipitate was suspended in boiling methanol, the suspension allowed to cool, and the solid filtered off and dried under high vacuum to give 3-amino-8-bromo-N,N-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonamide (0.708 g, 59%). 1H NMR (DMSO-d6, 200 MHz) δ: 1.07 (t, J=7 Hz, 6H, ethyl CH3), 2.54-2.62 (m, 2H, Ar CH2), 2.81-2.88 (m, 2H, Ar CH2), 3.26 (q, J=7 Hz, 4H, ethyl CH2), 6.83 (br s, 2H, NH2), 7.60(s, 1H, Ar), 9.13 (s, 1H, Ar), 10.95 (br s, 1H, NH). Anal Calculated for C16H19BrN4O3S: C,44.97; H,4.48; Br,18.70; N,13.11; S,7.50. Found: C,44.90; H,4.49; Br,18.65; N,13.03; S,7.57.

후처리

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. temperatureto cool
  4. filtrationthe solid filtered off
  5. customdried under high vacuum

출처 및 근거

ORD 기록
ord-1c87df6f3b704d6e8f71d27344289c30
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663337

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