Phosphorus oxychloride → HCID 86743349, compound

HRID 1607082Notes

Reaction equation

HRID 1607082 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][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[C:18]([S:23][CH3:24])[C:19]2=4)[NH:14][CH:13]=3)[N:9]([CH3:25])[CH2:8]1)=O)[CH3:2].P(Cl)(Cl)(Cl)=O.C(OC([S-])=[S:37])C.[K+]>C(Cl)Cl>[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][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[C:18]([S:23][CH3:24])[C:19]2=4)[NH:14][CH:13]=3)[N:9]([CH3:25])[CH2:8]1)=[S:37])[CH3:2]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 2735045Potassium ethylxanthateHCID 86743350HCID 86743350, compound

Product 1

HCID 86743349HCID 86743349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At -20° C., 5.79 g of 1,1-diethyl-3-(6-methyl-12-methylthio-8α-ergolinyl)urea (15 mmol) is dissolved in a mixture of 4.13 g of freshly distilled phosphorus oxychloride (45 mmol) and 50 ml of anhydrous methylene chloride and the temperature is allowed to rise within 4 hours to +10° C. The mixture is stirred overnight at room temperature and then another 2 hours at 40° C.,and the solvent is subsequently distilled off under vacuum. The residue is dissolved in 50 ml of anhydrous acetonitrile, cooled to -10° C., combined with 7.2 g of potassium ethylxanthate (45 mmol), and stirred at room temperature for 20 hours. The solvent is exhaustively removed by distillation; then the mixture is distributed between ethyl acetate and saturated sodium carbonate solution; the organic phase is dried with sodium sulfate and evaporated. The residue is crystallized from ethyl acetate, yielding 82%.

Workup

  1. distillationanother 2 hours at 40° C.,and the solvent is subsequently distilled off under vacuum
  2. dissolutionThe residue is dissolved in 50 ml of anhydrous acetonitrile
  3. temperaturecooled to -10° C.
  4. stirringstirred at room temperature for 20 hours
  5. customThe solvent is exhaustively removed by distillation
  6. dry with materialthe organic phase is dried with sodium sulfate
  7. customevaporated
  8. customThe residue is crystallized from ethyl acetate
  9. customyielding 82%

Sources & evidence

ORD record
ord-233366195e144ee8b8cbc23ff8909965
Source dataset
uspto-grants-1989_09
Patent number
US04863929

Reaction notes

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