Hydrochloric Acid → HCID 68662198、化合物

HRID 729261ノート

反応式

HRID 729261 の反応式
[F:1][CH:2]([F:22])[O:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][NH:9][S:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[C:23](OCC)(=[O:27])[C:24]([O-])=[O:25].CC(C)([O-])C.[K+].Cl>C1COCC1>[F:22][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:24](=[O:25])[C:23]([OH:27])=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:10]2(=[O:12])=[O:11])=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21943339Ethanedioic acid, monoethyl esterHCID 23665647Potassium tert-butoxideHCID 33038515N-[4-(Difluoromethoxy)benzyl]-1-phenylmethanesulfonamide

生成物 1

HCID 68662198HCID 68662198、化合物収率 90.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

N-[4-(Difluoromethoxy)benzyl]-1-phenylmethanesulfonamide (0.6 g, 1.83 mmol) and ethyl oxalate (0.32 g, 2.20 mmol) were mixed in THF (4 mL, dry). Under an atmosphere of nitrogen, potassium tert-butoxide (0.27 g, 2.38 mmol) was added and the reaction mixture was heated in a microwave reactor at 150° C. for 10 mins and then at 150° C. for 5 mins. The mixture was then cooled in an ice-bath and HCl (10%, 1 mL) was added, pH˜1. The mixture was evaporated to remove THF and the residue was extracted with DCM (20 mL). The extract was dried (MgSO4) and evaporated to give the crude product (0.634 g). It was used in the next step without further purification.

後処理

  1. temperatureThe mixture was then cooled in an ice-bath
  2. customThe mixture was evaporated
  3. customto remove THF
  4. extractionthe residue was extracted with DCM (20 mL)
  5. dry with materialThe extract was dried (MgSO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-745268b0a7df45b0a239785518ccb393
出典データセット
uspto-grants-2009_09
特許番号
US07582629B2

反応ノート

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