Methyl isothiocyanate → HCID 15586952, compound

HRID 225198Notes

Reaction equation

HRID 225198 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([CH2:18][NH:19][NH2:20])[CH2:3]1.[CH3:21][N:22]=[C:23]=[S:24]>O1CCCC1>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([CH2:18][NH:19][NH:20][C:23](=[S:24])[NH:22][CH3:21])[CH2:3]1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 15586932HCID 15586932, compound

Product 1

HCID 15586952HCID 15586952, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0.5 °C

Procedure

1.2 g (0.0043 moles) of 6-methyl-8β-hydrazinomethyl-ergoline are dissolved in 120 ml of dry tetrahydrofuran, the solution is cooled to 0.5° C., and 0.38 g (0.0052 moles) of methyl isothiocyanate are added with stirring. The reaction mixture is stirred for one hour, and the solvent is distilled off in vacuo. The residue is subjected to chromatography on a column packed with 40 g of silica gel; a 100:0.3:20 mixture of chloroform, water and methanol is applied as eluting agent. The eluents which contain a single compound with an Rf value of 0.45 are combined and evaporated, and the dry residue is crystallized from ethanol. 1.1 g (76.8%) of 6-methyl-8β-([N'-methylthiocarbamoyl-hydrazino]-methyl)-ergoline are obtained; m.p.: 220°-221° C., [α]D20 =-45.7° (c=1, in 96% ethanol).

Workup

  1. stirringThe reaction mixture is stirred for one hour
  2. distillationthe solvent is distilled off in vacuo
  3. additiona 100:0.3:20 mixture of chloroform, water and methanol
  4. washas eluting agent
  5. customevaporated
  6. customthe dry residue is crystallized from ethanol

Sources & evidence

ORD record
ord-6c03fd5277974af5891ac57fc8a33008
Source dataset
uspto-grants-1980_11
Patent number
US04235912

Reaction notes

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