Gamma-Butyrolactone → 5-(2-hydroxyethyl)-2-thiouracil

HRID 859949ノート

反応式

HRID 859949 の反応式
C(OCC)=O.[C:6]1(=[O:11])[O:10][CH2:9][CH2:8][CH2:7]1.[CH3:12]C(C)([O-])C.[K+].[NH2:18][C:19]([NH2:21])=[S:20]>CCOCC.O1CCCC1.CC(O)C>[OH:10][CH2:9][CH2:8][C:7]1[C:6](=[O:11])[NH:18][C:19](=[S:20])[NH:21][CH:12]=1

参加物

8

反応物 4

HCID 7302Gamma-ButyrolactoneHCID 8025Ethyl formateHCID 2723790ThioureaHCID 23665647Potassium tert-butoxide

生成物 1

HCID 36146775-(2-hydroxyethyl)-2-thiouracil

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of ethyl formate (33.1 ml, 2.1 equiv) and γ-butyrolactone (15 ml, 1 equiv) in ether (400 ml) was added dropwise with stirring to a solution of potassium t-butoxide (52.5 g, 2.4 equiv) in tetrahydrofuran (400 ml). The mixture was allowed to warm to room temperature, and stirred overnight. The solvent was removed in vacuo, 2-propanol (600 ml) and thiourea (29.7 g, 2 equiv) were added, and the mixture was heated to reflux for 5 h. After cooling to room temperature, the precipitate was filtered off, dissolved in water (500 ml), and washed twice with ether. The aqueous solution was acidified to pH5.5 with acetic acid, and the resulting precipitate was filtered off, washed thoroughly with water, and dried in vacuo; yield 23.85 g. 1H-NMR (d6-DMSO) δ 2.36 (2H, t), 3.47 (2H, m), 4.57 (1H, m), 7.24 (1H, s), 12.2 & 12.4 (each 1H, br s); MS (APCI−) found (M−H)=171; C6H8N2O2S requires 172.

後処理

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 5 h
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitate was filtered off
  6. dissolutiondissolved in water (500 ml)
  7. washwashed twice with ether
  8. filtrationthe resulting precipitate was filtered off
  9. washwashed thoroughly with water
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-da6e712bcc594b74b33c9d59b42acf10
出典データセット
uspto-grants-2006_12
特許番号
US07153861B2

反応ノート

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