Benzoyl isothiocyanate → HCID 13188272, compound

HRID 615687Notes

Reaction equation

HRID 615687 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH2:13][C@H:14]1[CH2:28][C@@H:27]2[C@@H:17]([CH2:18][C:19]3[C:29]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]2=4)[NH:21][CH:20]=3)[N:16]([CH3:30])[CH2:15]1>C(#N)C>[CH3:30][N:16]1[C@H:17]2[C@H:27]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:29]=3[C:19]([CH2:18]2)=[CH:20][NH:21]4)[CH2:28][C@H:14]([CH2:13][NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[S:11])[CH2:15]1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 12799440HCID 12799440, compound

Product 1

HCID 13188272HCID 13188272, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.05 ml of benzoyl isothiocyanate were added to a suspension of 2 g of 8α-aminomethyl-6-methyl-10β-ergoline in 22 ml of acetonitrile at 80° C. under shaking. The solution was refluxed for thirty minutes and then evaporated in vacuo to dryness. The residue was chromatographed on silica gel (eluant chloroform with 2% methanol) to give 2.2 g of the title compound, m.p. 153°-155° C., after crystallization from diethyl ether.

Workup

  1. temperatureThe solution was refluxed for thirty minutes
  2. customevaporated in vacuo to dryness
  3. customThe residue was chromatographed on silica gel (eluant chloroform with 2% methanol)

Sources & evidence

ORD record
ord-862d3c9c0bdb4861afbbfac75ebf8770
Source dataset
uspto-grants-1985_02
Patent number
US04500712

Reaction notes

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