Trifluoroacetic acid → 2-(Methylthio)-5,6,7,8-tetrahydroquinazolin-4(3H)-one

HRID 523477ノート

反応式

HRID 523477 の反応式
[CH3:1][S:2][C:3]1[N:12]=[C:11](N)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1.CC(C)CC[O:18]N=O.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl.ClCCl>[CH3:1][S:2][C:3]1[NH:12][C:11](=[O:18])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 8053Isoamyl NitriteHCID 127186294-Quinazolinamine, 5,6,7,8-tetrahydro-2-(methylthio)-

生成物 1

HCID 1354352562-(Methylthio)-5,6,7,8-tetrahydroquinazolin-4(3H)-one

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

2-Methylsulfanyl-5,6,7,8-tetrahydroquinazolin-4-ylamine (5.09 g; 23.145 mmol), 3-methyl-1-nitrosooxybutane (11.6 ml; 86.79 mmol) and trifluoroacetic acid (23.2 ml; 300.89 mmol) are dissolved in chloroform (300 ml), the pale-yellow solution is warmed to 60° C. and stirred for 2 h. The reaction mixture is diluted with dichloromethane and extracted with 10% K2CO3. The aqueous phase is separated off and back-extracted once with dichloromethane, NaCl is subsequently added, and the mixture is extracted again with ethyl acetate. The combined organic phases are dried over Na2SO4, filtered and evaporated. The crude product obtained in this way is adsorbed onto sorbent and purified by chromatography on a SI50 silica-gel column of a Combiflash Companion XL. After evaporation of the product fractions, the crystalline residue is triturated with diethyl ether, filtered off by suction and dried in vacuo; yield: 2.0 g (57%), crystals.

後処理

  1. extractionextracted with 10% K2CO3
  2. customThe aqueous phase is separated off
  3. extractionback-extracted once with dichloromethane, NaCl
  4. additionis subsequently added
  5. extractionthe mixture is extracted again with ethyl acetate
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-d8580725029e47c89504e0b92a088534
出典データセット
uspto-grants-2016_05
特許番号
US09339503B2

反応ノート

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