Lithium hydroxide, monohydrate → HCID 178481600, 화합물

HRID 1055811노트

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HRID 1055811 반응식
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](S(C)=O)[N:8]([CH3:15])[C:7]2=[O:16].IC1C=CC=C2C=1N=C(S(C)(=O)=[O:29])N(C)C2=O.O[Li].O>C1COCC1.O>[OH:29][C:9]1[N:8]([CH3:15])[C:7](=[O:16])[C:6]2[C:11](=[C:2]([I:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

참가 물질

6

반응물 3

HCID 168937Lithium hydroxide, monohydrateHCID 897820068-iodo-3-methyl-2-(methylsulfonyl)quinazolin-4(3H)-onHCID 897821678-iodo-3-methyl-2-(methylsulfinyl)quinazolin-4(3H)-one

생성물 1

HCID 178481600HCID 178481600, 화합물수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

A suspension of 8-iodo-3-methyl-2-(methylthio)quinazolin-4(3H)-one (700a; 15 g, 45.2 mmol) in 400 mL of DCM was set stirring at 0° C. before adding 3-chlorobenzoperoxoic acid (15.59 g of 77% max. Aldrich, 70 mmol) portion wise over 10 min. The ice bath was removed; and the reaction mixture was stirred at RT for 30 min. It was diluted with 200 mL of DCM, washed sequentially with ice cold 2×50 mL of saturated Na2CO3 followed by sat. Na2SO3 solution and 15 mL of brine. The organic solution was dried over Na2SO4, filtered, and concentrated under reduced pressure to give yellow crystalline solid (700b) containing a mixture of 8-iodo-3-methyl-2-(methylsulfinyl)quinazolin-4(3H)-one and 8-iodo-3-methyl-2-(methylsulfonyl)quinazolin-4(3H)-on. The crude material of yellow crystalline solid (700b) in 40 mL of THF and 40 mL of water at RT was treated with LiOH—H2O (6.60 g, 275 mmol). The reaction mixture was stirred in an oil bath at 75° C. for 2.5 h. It was concentrated to half of its volume under reduced pressure. The precipitated solid was filtered, rinsed with 2×5 mL of water followed by 2×5 mL of ether. The off-white crystalline solid was dried in a vacuum oven at 45° C. for 48 h to give 2-hydroxy-8-iodo-3-methylquinazolin-4(3H)-one (700c; 12.79 g, 42.3 mmol, 94% yield). The crude material was used in the next step. m/z (ES, +ve) 302.9 (M+H)+.

후처리

  1. additioncontaining
  2. concentrationIt was concentrated to half of its volume under reduced pressure
  3. filtrationThe precipitated solid was filtered
  4. washrinsed with 2×5 mL of water
  5. customThe off-white crystalline solid was dried in a vacuum oven at 45° C. for 48 h

출처 및 근거

ORD 기록
ord-f29ec58377534927915dfed00fc98c56
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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