Ammonia → 3-(2,3beta-Dihydro-6-methyl-1-methylthio-13-nitro-8alpha-ergolinyl)-1,1-diethylurea

HRID 1073301Notes

Reaction equation

HRID 1073301 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[C:9]([N+:18]([O-:20])=[O:19])[CH:10]=[C:11]4[C:17]=3[C@H:14]([CH2:15]2)[CH2:13][NH:12]4)[CH2:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1.F[B-](F)(F)F.[CH3:34][S+:35](C)SC.N>O1CCCC1>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[C:9]([N+:18]([O-:20])=[O:19])[CH:10]=[C:11]4[C:17]=3[C@H:14]([CH2:15]2)[CH2:13][N:12]4[S:35][CH3:34])[CH2:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2737114Dimethyl(methylthio)sulfonium tetrafluoroborateHCID 13374954HCID 13374954, compound

Product 1

HCID 867443363-(2,3beta-Dihydro-6-methyl-1-methylthio-13-nitro-8alpha-ergolinyl)-1,1-diethylureaYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 38 mg (0.1 mmol) of 3-(2,3β-dihydro-6-methyl-13-nitro-8α-ergolinyl)-1,1-diethylurea in 2 ml of absolute, freshly distilled tetrahydrofuran is combined with 47 mg (0.24 mmol) of dimethylmethylthiosulfonium fluoroborate, and the mixture is agitated for 20 minutes at room temperature. For working-up purposes, the batch is poured on 10 ml of ice and rendered alkaline with 25% strength ammonia solution. The organic phase is extracted repeatedly with methylene chloride. The extracts are dried over magnesium sulfate and concentrated. The crude product is purified over a preparative silica gel plate with methylene chloride/methanol 9:1 as the eluent, thus obtaining 28 mg of 3-(2,3β-dihydro-6-methyl-1-methylthio-13-nitro-8α-ergolinyl)-1,1-diethylurea.

Workup

  1. extractionThe organic phase is extracted repeatedly with methylene chloride
  2. dry with materialThe extracts are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified over a preparative silica gel plate with methylene chloride/methanol 9:1 as the eluent

Sources & evidence

ORD record
ord-f4a2097aca7741f9ba087216961d9533
Source dataset
uspto-grants-1990_11
Patent number
US04968801

Reaction notes

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