Potassium Hydroxide → HCID 86743347, compound

HRID 1607080Notes

Reaction equation

HRID 1607080 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[C:4](=[O:26])[NH:5][C@H:6]1[CH2:20][C@H:19]2[C@@H:9]([CH2:10][C:11]3[C:21]4[C:14](=[CH:15][CH:16]=[C:17]([C:22]([NH2:24])=O)[C:18]2=4)[NH:13][CH:12]=3)[N:8]([CH3:25])[CH2:7]1)[CH3:2].P(Cl)(Cl)(Cl)=O.[OH-].[K+]>C(Cl)(Cl)Cl>[C:22]([C:17]1[C:18]2=[C:21]3[C:14]([NH:13][CH:12]=[C:11]3[CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][C@H:6]([NH:5][C:4](=[O:26])[N:3]([CH2:27][CH3:28])[CH2:1][CH3:2])[CH2:7][N:8]3[CH3:25])=[CH:15][CH:16]=1)#[N:24]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 70394938HCID 70394938, compound

Product 1

HCID 86743347HCID 86743347, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

383 mg of [8α-(3,3-diethylureido)-6-methylergolin-12-yl]carboxylic acid amide (1 mmol) is dissolved in 25 ml of chloroform, 3 ml of phosphorus oxychloride is added thereto, and the mixture is agitated for 16 hours at 55° C. The mixture is poured on ice, allowed to stand for 30 minutes, then made alkaline with 1N potassium hydroxide solution, and extracted with methylene chloride. The organic phase is dried with sodium sulfate and evaporated. The residue is crystallized from ethyl acetate in a 43% yield. [α]D =+16° (0.5% in chloroform).

Workup

  1. additionThe mixture is poured on ice
  2. waitto stand for 30 minutes
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic phase is dried with sodium sulfate
  5. customevaporated
  6. customThe residue is crystallized from ethyl acetate in a 43% yield
  7. custom[α]D =+16° (0.5% in chloroform)

Sources & evidence

ORD record
ord-36d24f3e779c434b8f5b1fcc1e509e7a
Source dataset
uspto-grants-1989_09
Patent number
US04863929

Reaction notes

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