Acetyl chloride → 3-(1-Acetyl-6-methyl-13-nitro-8alpha-ergolinyl)-1,1-diethylurea

HRID 35219Notes

Reaction equation

HRID 35219 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:19]3[C:9]([CH2:10][C@@H:11]4[C@@H:16]([C:17]=3[CH:18]=1)[CH2:15][C@H:14]([NH:20][C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:13][N:12]4[CH3:28])=[CH:8][NH:7]2)([O-:3])=[O:2].[C:29](Cl)(=[O:31])[CH3:30].[OH-].[K+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>[C:29]([N:7]1[C:6]2[C:19]3[C:9]([CH2:10][C@@H:11]4[C@@H:16]([C:17]=3[CH:18]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:15][C@H:14]([NH:20][C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:13][N:12]4[CH3:28])=[CH:8]1)(=[O:31])[CH3:30]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 14797Potassium HydroxideHCID 133749573-(13-Nitro-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 867423593-(1-Acetyl-6-methyl-13-nitro-8alpha-ergolinyl)-1,1-diethylurea

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution is prepared from 410 mg of 3-(13-nitro-6-methyl-8α-ergolinyl)-1,1-diethylurea in 10 ml of methylene chloride, 40 mg of tetrabutylammonium hydrogen sulfate and 0.8 ml of acetyl chloride are added, and this mixture is poured on 1 g of pulverized potassium hydroxide. After 1.5 hours of agitation at room temperature, the mixture is diluted with sodium bicarbonate solution, the organic phase is separated and dried with sodium sulfate. After evaporation and chromatography as indicated in Example 9, 375 mg of 3-(1-acetyl-6-methyl-13-nitro-8α-ergolinyl)-1,1-diethylurea is obtained.

Workup

  1. additionare added
  2. customthe organic phase is separated
  3. dry with materialdried with sodium sulfate
  4. customAfter evaporation and chromatography

Sources & evidence

ORD record
ord-8a99252617924af7b5e6e37583a9b8a9
Source dataset
uspto-grants-1988_08
Patent number
US04766128

Reaction notes

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