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

HRID 539855노트

반응식

HRID 539855 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-708f99d0e44144b38e79df2e6dd543db
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871775B2

반응 노트

불러오는 중…