Reaction #63493

ord-b8a17eee9b8649738d7245eacbbd1a9e

Reaction equation

CC[O-].[Na+]
sodium ethylate
CC(C)(C)OCl
tert-butyl hypochlorite
CCN(CC)C(=O)N[C@@H]1C[C@@H]2c3cc([N+](=O)[O-])cc4c3C(CN4)C[C@H]2N(C)C1
3-(2,3-dihydro-6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea
CSC
dimethyl sulfide
CCN(CC)CC
triethylamine
→
CCN(CC)C(=O)N[C@@H]1C[C@@H]2c3cc([N+](=O)[O-])cc4[nH]cc(c34)C[C@H]2N(C)C1
3-(6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea
Yield 25.9%

Reactants

CC[O-].[Na+]
sodium ethylate
CC(C)(C)OCl
tert-butyl hypochlorite
CCN(CC)C(=O)N[C@@H]1C[C@@H]2c3cc([N+](=O)[O-])cc4c3C(CN4)C[C@H]2N(C)C1
3-(2,3-dihydro-6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea
CSC
dimethyl sulfide
CCN(CC)CC
triethylamine

Reagents

None

Solvents

CCO
ethanol
O
water
ClCCl
methylene chloride
ClCCl
methylene choride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.WAITwithin 10 minutes
  2. 2
    Extractionextracted with methylene chloride
  3. 3
    Otherthe organic phase is dried
  4. 4
    Otherevaporated

Procedure

A solution of 0.4 mmol of tert-butyl hypochlorite in 2 ml of methylene chloride is added dropwise to a solution of 0.3 mmol of 3-(2,3-dihydro-6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea, 0.4 mmol of dimethyl sulfide, and 0.3 mmol of triethylamine in 5 ml of methylene choride at -70° C., and the mixture is agitated for 2 hours. Then a solution of 2 mmol of sodium ethylate in 2 ml of ethanol is added thereto within 10 minutes, and the mixture is warmed up to room temperature within 2 hours, whereafter it is combined with water, extracted with methylene chloride, the organic phase is dried and evaporated. Chromatography on silica gel with methylene chloride/methanol (5%) yields 30 mg of 3-(6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04766128uspto-grants-1988_08