Benzene → 2,3-Dihydroperimidine

HRID 963123

반응식

HRID 963123 반응식
OC[C:3]1(CO)[NH:14][C:13]2[C:15]3[C:9]([CH:10]=[CH:11][CH:12]=2)=[CH:8][CH:7]=[CH:6][C:5]=3[NH:4]1.C1C=CC=CC=1.[OH-].[Na+].BrCC(OC(C)(C)C)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[NH:4]1[C:5]2=[C:15]3[C:9](=[CH:8][CH:7]=[CH:6]2)[CH:10]=[CH:11][CH:12]=[C:13]3[NH:14][CH2:3]1

참가 물질

7

반응물 4

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 111955781H-Perimidine-2,2(3H)-dimethanol

생성물 1

HCID 124409652,3-Dihydroperimidine수율 127.3%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매

실험 절차

A mixture of 2,2-bis(hydroxymethyl)-2,3-dihydro-1H-perimidine (4.14 g, 18.0 mmol), benzene (45 mL), 50% aqueous sodium hydroxide (37.5 mL), tetrabutylammonium hydrogen sulfate (1.0 g, 2.94 mmol), and t-butyl bromoacetate (5.85 mL, 39.6 mmol) was vigorously stirred at room temperature for 18 hours using a mechanical stirrer. The reaction mixture was diluted with water (150 mL) and then extracted twice with chloroform (150 mL each). The chloroform extracts were combined and washed with brine (100 mL). The chloroform layer was dried using anhydrous magnesium sulfate, filtered, and then concentrated to give a tan solid. The solid was recrystallized with methanol to yield 3.90 g of 1,3-dihydroperimidine derivative I as tan crystals; m.p. 152°-154° C.; 1H NMR (500 Mz; CDCl3): δ 1.46 (s, 18H); 3.70 (s, 4H); 4.01 (s, 5H); 5.20 (s, 2H); 6.51 (δ, 2H, J=7.3 Hz); 7.12 (δ, 2H, J=8.Hz); 7.21 (t, 2H, J=7.8 Hz); 13C{1H} NMR (125 Mz; CDCl3): δ 28.00, 67.09, 69.43, 72.53, 81.75, 105.88, 112.33, 116.87, 126.92, 134.34, 138.74, 169.56.

후처리

  1. extractionextracted twice with chloroform (150 mL each)
  2. washwashed with brine (100 mL)
  3. dry with materialThe chloroform layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a tan solid
  7. customThe solid was recrystallized with methanol

출처 및 근거

ORD 기록
ord-0b53764952f449d19707a7120fc2eb5d
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763134

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