Hydrochloric Acid → 5-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-3-methyl-sulphanyl-1,3-dihydro-indol-2-one

HRID 44291

反応式

HRID 44291 の反応式
C(OC(=O)C[S:6]C)C.[NH2:9][C:10]1[CH:30]=[CH:29][C:13]([CH2:14][N:15]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:18][O:17][C:16]2=[O:28])=[CH:12][CH:11]=1.[C:31]([O:35]Cl)(C)(C)C.C(N([CH2:42][CH3:43])CC)C.Cl>C1COCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[CH2:18][O:17][C:16](=[O:28])[N:15]([CH2:14][C:13]3[CH:29]=[C:30]4[C:10](=[CH:11][CH:12]=3)[N:9]([SH:6])[C:31](=[O:35])[CH:42]4[CH3:43])[N:20]=2)=[CH:22][CH:23]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochloriteHCID 666364683-(4-Amino-benzyl)-5-(4-chloro-phenyl)-3,6-dihydro-[1,3,4]oxadiazin-2-one

生成物 1

HCID 866624325-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-3-methyl-sulphanyl-1,3-dihydro-indol-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-60 °C

実験手順

Ethyl(methylsulphanyl)acetate (27.31 mmoles) is added dropwise to a solution of the compound obtained in Step E (23.75 mmoles) in THF (200 ml) at −60° C. under a nitrogen atmosphere. tBuOCl (27.31 mmoles) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for 3 hours at −60° C., triethylamine (29.68 mmoles) is added dropwise. The reaction mixture is brought to ambient temperature; aqueous 3M HCl solution (340 ml) is then added and stirring is carried out for a further 2 hours. The organic phase is evaporated and the aqueous suspension is extracted with DCM. The organic phases are combined, then washed with 2M HCl solution and then with saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue is triturated in ethyl ether, filtered and dried in vacuo to yield the title product, which is used directly in the next Step.

後処理

  1. customthe temperature between −60° C. and −55° C
  2. customis brought to ambient temperature
  3. stirringstirring
  4. waitis carried out for a further 2 hours
  5. customThe organic phase is evaporated
  6. extractionthe aqueous suspension is extracted with DCM
  7. washwashed with 2M HCl solution
  8. dry with materialwith saturated NaCl solution, dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue is triturated in ethyl ether
  12. filtrationfiltered
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-8253b3b8bacd438ab0b3414223283023
出典データセット
uspto-grants-2013_09
特許番号
US08541412B2

関連ノート

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