Ammonia → HCID 86743351, compound

HRID 1607083Notes

Reaction equation

HRID 1607083 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][CH:12]3[C:22]4[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=O)[C:19]2=4)[NH:14][CH2:13]3)[N:9]([CH3:25])[CH2:8]1)=[O:5])[CH3:2].[NH2:28]OS(O)(=O)=O.N>O>[C:23]([C:18]1[C:19]2=[C:22]3[C:15]([NH:14][CH2:13][CH:12]3[CH2:11][C@@H:10]3[C@@H:20]2[CH2:21][C@H:7]([NH:6][C:4](=[O:5])[N:3]([CH2:1][CH3:2])[CH2:26][CH3:27])[CH2:8][N:9]3[CH3:25])=[CH:16][CH:17]=1)#[N:28]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 76284hydroxylamine-O-sulfonic acidHCID 86743352HCID 86743352, compound

Product 1

HCID 86743351HCID 86743351, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 500 mg of 1,1-diethyl-3-(2,3-dihydro-12-formyl-6-methyl-8α-ergolinyl)urea and 460 mg of hydroxylamine-O-sulfonic acid in 5 ml of water is stirred for 20 hours at room temperature. The reaction mixture is poured on ice, set to be alkaline with 25% strength ammonia solution, and extracted with dichloromethane. The organic phase is dried (Na2SO4), concentrated, the residue chromatographed on silica gel with dichloromethane/methanol=95/5 as the eluting agent, and crystallized from ethyl acetate/pentane. Yield 26% of theory.

Workup

  1. additionThe reaction mixture is poured on ice
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue chromatographed on silica gel with dichloromethane/methanol=95/5 as the eluting agent
  6. customcrystallized from ethyl acetate/pentane

Sources & evidence

ORD record
ord-e5806cfbd5dc414e8ec7ecd016317fcd
Source dataset
uspto-grants-1989_09
Patent number
US04863929

Reaction notes

Loading…