Sodium Hydroxide → 1-(3-Methoxybenzyl)-3-Octadecyl Thiourea

HRID 1375750ノート

反応式

HRID 1375750 の反応式
Cl.[CH2:2]([NH2:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Na+].C(N)CCCCCCCCCCCCCCCCC.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:51]=[CH:52][CH:53]=1)[CH2:47][N:48]=[C:49]=[S:50].[N-]=C=S>C(O)C.CCOCC>[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:51]=[CH:52][CH:53]=1)[CH2:47][NH:48][C:49]([NH:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[S:50]

参加物

8

反応物 5

HCID 14798Sodium HydroxideHCID 15793Octadecylamine2 回HCID 1265123-Methoxybenzyl isothiocyanateHCID 519552Stearamine hydrochlorideHCID 178418790HCID 178418790、化合物

生成物 1

HCID 120820551-(3-Methoxybenzyl)-3-Octadecyl Thiourea

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
4 °C

実験手順

Octadecyl amine hydrochloride was converted to the amine by mixing an ether solution of the amine hydrochloride with 1 M NaOH, separating and evaporating the ether layer, dissolving the amine in CHCl3, filtering through Whatman 541 filter paper and evaporating the CHCl3. Octadecyl amine (5.9252 g, 22.0 mmol) in 150 ml ethanol was reacted with an excess (4.32 g, 24.1 mmol) of 3-methoxybenzyl isothiocyanate at 40° C. under N2 with stirring. Excess isothiocyanate was used because co-crystallization of octadecyl amine is difficult to prevent when an excess of amine is present. After 2 h the solution was cooled to 4° C., centrifuged at 10,000 rpm for 20 min and the precipitated crystals were washed with ethanol (20 ml). The combined supernatant and wash was evaporated to 20 ml total volume and then cooled to −10° C. to filter off a second batch of crystals. The supernatant was dried and 94.3% of reagents weight was recovered, 74.9%, or 7.40 g as 1-(3-methoxybenzyl)-3-(octadecyl) thiourea of about 76% purity based on the sulfur analysis. The octadecyl amine was difficult to separate from the thiourea by crystallization. Calculated elemental analysis of 1-(3-methoxybenzyl)-3-octadecyl thiourea: C, 72.27; H, 10.78; N, 6.24; S, 7.15. Found: C, 71.96; H, 11.00; N, 5.95; S, 5.46. A recrystallization from acetone/chloroform gave crystals with the composition: C, 72.37; H, 10.98; N, 6.13; S, 6.92.

後処理

  1. customseparating
  2. customevaporating the ether layer
  3. dissolutiondissolving the amine in CHCl3
  4. filtrationfiltering through Whatman 541
  5. filtrationfilter paper
  6. customevaporating the CHCl3
  7. washthe precipitated crystals were washed with ethanol (20 ml)
  8. washThe combined supernatant and wash
  9. customwas evaporated to 20 ml total volume
  10. temperaturecooled to −10° C.
  11. filtrationto filter off a second batch of crystals
  12. customThe supernatant was dried
  13. custom94.3% of reagents weight was recovered
  14. customto separate from the thiourea by crystallization
  15. customA recrystallization from acetone/chloroform
  16. customgave crystals with the composition

出典と根拠

ORDレコード
ord-3d58813736d741e88b0095e000f09a71
出典データセット
uspto-grants-2007_01
特許番号
US07169815B2

反応ノート

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