Ammonia → HCID 86742343, compound

HRID 35209Notes

Reaction equation

HRID 35209 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[CH:14]([CH2:15]2)[CH2:13][NH:12]4)[CH2:5][C@H:4]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3]1.[N+:26]([O-])([OH:28])=[O:27].N>S(=O)(=O)(O)O>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[C:9]([N+:26]([O-:28])=[O:27])[CH:10]=[C:11]4[C:17]=3[CH:14]([CH2:15]2)[CH2:13][NH:12]4)[CH2:5][C@H:4]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 944Nitric AcidHCID 86742344HCID 86742344, compound

Product 1

HCID 86742343HCID 86742343, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Under ice cooling, 10 mmol of 3-(2,3-dihydro-6-methyl-8α-ergolinyl)-1,1-diethylurea is dissolved in 100 ml of concentrated sulfuric acid; 7 ml of a solution of 10 ml of 65% nitric acid in 90 ml of concentrated sulfuric acid is added thereto, and the mixture is stirred for 15 minutes in an ice bath. The reaction solution is then slowly introduced dropwise into ice, made alkaline under ice cooling with 32% ammonia solution, and extracted by shaking with methylene chloride. After washing the organic phase with water and drying with magnesium sulfate, the nitrated compound is obtained in a 90% crude yield. After chromatographic separation and purification, respectively, 3-(2,3-dihydro-6-methyl-13-nitro-8α-ergolinyl)-1,1-diethylurea is obtained in a 71% yield.

Workup

  1. additionThe reaction solution is then slowly introduced dropwise into ice
  2. extractionextracted
  3. stirringby shaking with methylene chloride
  4. washAfter washing the organic phase with water
  5. dry with materialdrying with magnesium sulfate
  6. customthe nitrated compound is obtained in a 90% crude yield
  7. customAfter chromatographic separation and purification

Sources & evidence

ORD record
ord-d032c1e579ee47058e10d5cedc10cce8
Source dataset
uspto-grants-1988_08
Patent number
US04766128

Reaction notes

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