Hydrochloric Acid → 2-Methylthieno[2,3-c]pyridine

HRID 254437ノート

反応式

HRID 254437 の反応式
CO[CH:3](OC)[CH2:4][N:5]([CH2:16][C:17]1[S:18][C:19]([CH3:22])=[CH:20][CH:21]=1)S(C1C=CC(C)=CC=1)(=O)=O.Cl.[OH-].[Na+].O.C([O-])(O)=O.[Na+]>O1CCOCC1.CCOCC>[CH3:22][C:19]1[S:18][C:17]2=[CH:16][N:5]=[CH:4][CH:3]=[C:21]2[CH:20]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23719242Sodium hydroxide--water (1/1/1)HCID 66859761N-(2,2-Dimethoxy-ethyl)4-methyl-N-(5-methyl-thiophen-2-ylmethyl)-benzenesulfonamide

生成物 1

HCID 121308462-Methylthieno[2,3-c]pyridine収率 58.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
107.5 °C

実験手順

76059-85: N-(2,2-Dimethoxy-ethyl)4-methyl-N-(5-methyl-thiophen-2-ylmethyl)-benzenesulfonamide (2) (50.56 g crude) was dissolved in dioxane (250 mL) and conc. HCl (200 mL) was added cautiously. The dark red solution was heated at gentle reflux (105 to 110° C.) for 24 hours. The volume was reduced by approximately half, then diluted with ether (200 mL). The pH was adjusted to between 7 and 8 using 50% NaOH/H2O and sat NaHCO3 solution with cooling. More ether (400 mL) was added, the mixture was filtered to remove insoluble material and the phases separated. The organic phase was washed with water (2×350 mL), dried (MgSO4) and condensed to dark red-brown oil. Purification was accomplished using Kugelrohr distillation (120 to 130° C.) to give 11.89 g of title compound as a pale yellow liquid.

後処理

  1. temperatureThe dark red solution was heated
  2. temperaturewith cooling
  3. filtrationthe mixture was filtered
  4. customto remove insoluble material
  5. customthe phases separated
  6. washThe organic phase was washed with water (2×350 mL)
  7. customdried
  8. custom(MgSO4) and condensed to dark red-brown oil
  9. customPurification
  10. distillationKugelrohr distillation (120 to 130° C.)

出典と根拠

ORDレコード
ord-1175847722df4fae85cc289fd7096087
出典データセット
uspto-grants-2011_01
特許番号
US07875627B2

反応ノート

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