Hydrochloric Acid → 7-Ethyl-2,3-dioxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine-6-carboxylic acid

HRID 1974973ノート

反応式

HRID 1974973 の反応式
C([O:3][C:4]([C:6]1[S:16][C:9]2[NH:10][C:11](=[O:15])[C:12](=[O:14])[NH:13][C:8]=2[C:7]=1[CH2:17][CH3:18])=[O:5])C.[OH-].[Na+].Cl.O>O1CCCC1>[C:4]([C:6]1[S:16][C:9]2[NH:10][C:11](=[O:15])[C:12](=[O:14])[NH:13][C:8]=2[C:7]=1[CH2:17][CH3:18])([OH:5])=[O:3]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19100738HCID 19100738、化合物

生成物 1

HCID 191007307-Ethyl-2,3-dioxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine-6-carboxylic acid収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of 6-ethoxycarbonyl-7-ethylthieno[2,3-b]-pyrazine-2,3(1H,4H)-dione (24.5 g, 91 mmol) and sodium hydroxide (10.96 g, 274 mmol) in 50% aqueous tetrahydrofuran (340 ml) was heated at 50°-60° C. for 16 h. The reaction mixture was cooled to 0° C. and acidified (pH=2) with hydrochloric acid. Water (300 ml) was added, the precipitate filtered off, washed with water and dried. Purification was performed by dissolving in 2 M sodium hydroxide solution, extraction with dichloromethane and precipitation of the aqueous phase with hydrochloric acid. The precipitate was filtered off, washed with water and dried to afford 14.2 g (65%) of the title compound. M.p. 230°-232° C. 1H-NMR (DMSO-d6, δ) : 1. 09 (t, 3H) 3.03 (q, 2H), 11.90 (s, 1H), 12.50 (br. s, 1H), 12.92 (br. s, 1H).

後処理

  1. temperaturewas heated at 50°-60° C. for 16 h
  2. filtrationthe precipitate filtered off
  3. washwashed with water
  4. customdried
  5. customPurification
  6. dissolutionby dissolving in 2 M sodium hydroxide solution
  7. extractionextraction
  8. customwith dichloromethane and precipitation of the aqueous phase with hydrochloric acid
  9. filtrationThe precipitate was filtered off
  10. washwashed with water
  11. customdried

出典と根拠

ORDレコード
ord-b31c7dc688a745e4adf4b86aef5bf2e3
出典データセット
uspto-grants-1994_02
特許番号
US05284847

反応ノート

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