Acetyl chloride → 1,1-Diethyl-3-(2-iodo-1-acetyl-6-methyl-8alpha-ergolinyl)urea

HRID 2352072Notes

Reaction equation

HRID 2352072 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][C:13]=3[I:23])[N:9]([CH3:24])[CH2:8]1)=[O:5])[CH3:2].[C:27](Cl)(=[O:29])[CH3:28].[OH-].[K+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[N:14]([C:27](=[O:29])[CH3:28])[C:13]=3[I:23])[N:9]([CH3:24])[CH2:8]1)=[O:5])[CH3:26]

Participants

7

Reactant 4

HCID 6367Acetyl chloride2×HCID 14797Potassium Hydroxide2×HCID 516892Sodium BicarbonateHCID 135590301,1-Diethyl-3-(2-iodo-6-methyl-8alpha-ergolinyl)urea

Product 1

HCID 137992231,1-Diethyl-3-(2-iodo-1-acetyl-6-methyl-8alpha-ergolinyl)urea

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

1.05 g of 1,1-diethyl-3-(2-iodo-6-methyl-8α-ergolinyl)urea is stirred for 3 hours at room temperature in 90 ml of methylene chloride with 115 mg of tetrabutylammonium hydrogen sulfate, 0.18 ml of acetyl chloride and 139 mg of pulverized potassium hydroxide pellets. After suctioning off over kieselguhr, the mixture is once again combined with the same amounts of acetyl chloride, pulverized potassium hydroxide and tetrabutylammonium hydrogen sulfate and stirred for one hour at room temperature. After combining with ice water, the mixture is neutralized with sodium bicarbonate and extracted by shaking. The organic phase is dried, filtered, and concentrated. The residue is chromatographed over silica gel with methylene chloride:ethanol=10:1 as the eluent, thus obtaining 500 mg of 1,1-diethyl-3-(2-iodo-1-acetyl-6-methyl-8α-ergolinyl)urea as an oil. [α]D =+40° (c=0.2 pyridine).

Workup

  1. extractionextracted
  2. stirringby shaking
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel with methylene chloride

Sources & evidence

ORD record
ord-8a988d0064294067a63ba4c14535c847
Source dataset
uspto-grants-1989_10
Patent number
US04874768

Reaction notes

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