Benzyl mercaptan → 7-(benzylthio)quinazolin-4(3H)-one

HRID 1473407노트

반응식

HRID 1473407 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:55]([SH:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.CCN(C(C)C)C(C)C>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:55]([S:62][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

참가 물질

8

반응물 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

생성물 1

HCID 1364090647-(benzylthio)quinazolin-4(3H)-one

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

A round bottom flask was charged with 7-bromoquinazolin-4(3H)-one (10 g, 44.4 mmol), Xantphos (1.286 g, 2.222 mmol), and Pd2(dba)3 (1.017 g, 1.111 mmol). The flask was flushed with Ar (g), then dioxane (89 ml), benzyl mercaptan (5.52 ml, 46.7 mmol), and n,n-diisopropylethylamine (15.52 ml, 89 mmol) were added in sequence. The reaction was fitted with a reflux condenser, heated to 90° C., and stirred for one hour. The reaction was diluted with water and filtered. The solids were washed thoroughly with water, then air dried for several hours and triturated with ethyl acetate. After stirring overnight, the solids were filtered, washed with ethyl acetate, and vacuum dried over a nitrogen blanket overnight to afford 7-(benzylthio)quinazolin-4(3H)-one as a light yellow solid. (ESI) 269.1 (M+H)+.

후처리

  1. customThe flask was flushed with Ar (g)
  2. customThe reaction was fitted with a reflux condenser
  3. filtrationfiltered
  4. washThe solids were washed thoroughly with water
  5. customair dried for several hours
  6. customtriturated with ethyl acetate
  7. stirringAfter stirring overnight
  8. filtrationthe solids were filtered
  9. washwashed with ethyl acetate, and vacuum
  10. customdried over a nitrogen blanket overnight

출처 및 근거

ORD 기록
ord-85789a104b724511b348466ea575a23e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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