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Triethylamine → 3-(2,6-Dichloro-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

HRID 1956700
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HRID 1956700 반응식
Cl.[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.C([O:23][C:24]1[C:25](=[O:35])[C:26](=O)[C:27]=1[NH:28][C:29]([CH3:33])([CH3:32])[CH2:30][CH3:31])CCC>O1CCCC1>[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5][NH:6][C:26]1[C:25](=[O:35])[C:24](=[O:23])[C:27]=1[NH:28][C:29]([CH3:32])([CH3:33])[CH2:30][CH3:31]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dioneHCID 16644432(2,6-Dichlorophenyl)methanamine hydrochloride

생성물 1

HCID 104974003-(2,6-Dichloro-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione수율 44.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 2,6-dichlorobenzylamine hydrochloride of Example 4, Step 2 (1.06 g 5.0 mmol) in tetrahydrofuran (10 mL) was added triethyl amine (0.505 g, 5.0 mmol) followed by 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1.20 g, 5.0 mmol, Example 3) and stirring was continued at room temperature for approximately 16 hours. The reaction mixture was freed of solvent and the residue was triturated successively with water and with diethyl ether, and then dried. The resulting light yellow solid was recrystallized from acetonitrile three times to provide 0.755 g (44%) of the title compound as a white solid: mp 239°-241° C. (dec); 1H NMR (DMSO-d6): δ7.57 (m, 1H), 7.55 (m, 1H), 7.52 (br m, 1H),m 7.43 (m, 1H), 7.30 (s, br, 1H), 5.07 (d, 2H), 1.65 (q, 2H), 1.28 (s, 6H), 0.80 (t, 3H) ppm. IR (KBr): 3250, 1785, 1660 cm-1 ; MS (m/z) 340/342/344 (M+). HPLC indicates a major component (99.7%).

후처리

  1. customthe residue was triturated successively with water and with diethyl ether
  2. customdried
  3. customThe resulting light yellow solid was recrystallized from acetonitrile three times

출처 및 근거

ORD 기록
ord-ae7635c53e82473e9cba53e8ed3c61f4
출처 데이터셋
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05780505

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