Bicarbonate Ion → 1,1-Diethyl-3-(1,6-dimethyl-2-methylthio-8alpha-ergolinyl)urea

HRID 2352067Notes

Reaction equation

HRID 2352067 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)[N:14]([CH3:23])[CH:13]=3)[N:9]([CH3:24])[CH2:8]1)=[O:5])[CH3:2].F[B-](F)(F)F.[CH3:32][S+:33](C)SC.F[B-](F)(F)F.[H+].C(=O)(O)[O-]>C1COCC1.C(Cl)Cl>[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]([CH3:23])[C:13]=3[S:33][CH3:32])[N:9]([CH3:24])[CH2:8]1)=[O:5])[CH3:26]

Participants

7

Reactant 4

HCID 769Bicarbonate IonHCID 28118Tetrafluoroboric acidHCID 2737114Dimethyl(methylthio)sulfonium tetrafluoroborateHCID 136545951,1-Diethyl-3-(1,6-dimethyl-8alpha-ergolinyl)urea

Product 1

HCID 137992211,1-Diethyl-3-(1,6-dimethyl-2-methylthio-8alpha-ergolinyl)urea

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution is prepared from 354 mg of 1,1-diethyl-3-(1,6-dimethyl-8α-ergolinyl)urea (1 mmol) in 20 ml of THF and, at room temperature under nitrogen, 392 mg of dimethylmethylthiosulfonium tetrafluoroborate (2 mmol) and 0.24 ml of 50% strength tetrafluoroboric acid are added thereto. After 30 minutes of agitation at room temperature, the mixture is distributed between methylene chloride and bicarbonate solution, the organic phases are combined, dried with sodium sulfate, and evaporated. The crude product is chromatographed with methylene chloride on silica gel yielding, after crystallization, 276 mg (69% of theory). [α]D =+11° (0.5% in chloroform).

Workup

  1. dry with materialdried with sodium sulfate
  2. customevaporated
  3. customThe crude product is chromatographed with methylene chloride on silica gel yielding
  4. customafter crystallization, 276 mg (69% of theory)
  5. custom[α]D =+11° (0.5% in chloroform)

Sources & evidence

ORD record
ord-2c9f62b0ae264295b395fa70571fdb1f
Source dataset
uspto-grants-1989_10
Patent number
US04874768

Reaction notes

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