Triethylamine → N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-pyridylmethyl)ethyl]thiourea

HRID 47696

反応式

HRID 47696 の反応式
C(N(CC)CC)C.[C:8]([N:12]=[C:13]=[S:14])([CH3:11])([CH3:10])[CH3:9].Cl.Cl.[NH2:17][C@H:18]([CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH2:19][OH:20]>C(O)C.C(OCC)(=O)C.O.ClCCl>[C:8]([NH:12][C:13]([NH:17][C@H:18]([CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH2:19][OH:20])=[S:14])([CH3:11])([CH3:10])[CH3:9]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 11544tert-Butyl isothiocyanateHCID 69885129(2R)-2-amino-3-(3-pyridyl)-1-propanol dihydrochloride

生成物 1

HCID 86584417N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-pyridylmethyl)ethyl]thiourea

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

22.7 cm3 of triethylamine and then 14 cm3 of tert-butyl isothiocyanate are added dropwise to a suspension, under an inert atmosphere, of 16.51 g of (2R)-2-amino-3-(3-pyridyl)-1-propanol dihydrochloride in 200 cm3 of ethanol. The mixture is then heated at a temperature in the region of 60° C. for 1 hour 30 min. After cooling to a temperature in the region of 20° C., the insoluble material is filtered off on a sinter funnel and the filtrate is then evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. A yellow paste is obtained, and is taken up in 200 cm3 of ethyl acetate and 100 cm3 of water. The aqueous phase is extracted and then washed with twice 200 cm3 of ethyl acetate. The organic phases are combined, washed with 3 times 50 cm3 of saturated sodium chloride solution and dried over magnesium sulfate. After filtration and then evaporation under reduced pressure (2 kPa) at a temperature in the region of 40° C., a yellow oil is obtained, which is taken up in dichloromethane and re-evaporated to give 3.25 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(3-pyridylmethyl)-ethyl]thiourea in the form of a pale yellow foam: [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 1.41 (s: 9H); 2.84 (mt: 2H); 3.37 (mt: 2H); 4.43 (unres. mult.: 1H); 4.96 (t, J=5 Hz: 1H); 7.24 (d, J=8 Hz: 1H); 7.27 (broad s: 1H); 7.33 (dd, J=8 and 5 Hz: 1H); 7.67 (dt, J=8 and 2 Hz: 1H); 8.42 (dd, J=5 and 2 Hz: 1H); 8.46 (d, J=2 Hz: 1H)].

後処理

  1. temperatureAfter cooling to a temperature in the region of 20° C.
  2. filtrationthe insoluble material is filtered off on a sinter funnel
  3. customthe filtrate is then evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C
  4. customA yellow paste is obtained
  5. extractionThe aqueous phase is extracted
  6. washwashed with twice 200 cm3 of ethyl acetate
  7. washwashed with 3 times 50 cm3 of saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtration
  10. customevaporation under reduced pressure (2 kPa) at a temperature in the region of 40° C.
  11. customa yellow oil is obtained
  12. customre-evaporated

出典と根拠

ORDレコード
ord-7917000d2526400bb72eb01cf21d36ff
出典データセット
uspto-grants-2004_03
特許番号
US06699895B2

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