Water → 1,1-Diethyl-3-(6-methyl-2-formyl-8alpha-ergolinyl)urea

HRID 2352070Notes

Reaction equation

HRID 2352070 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4]([NH:6][CH: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[CH:23]2SCCS2)[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:2].O.S(Cl)(Cl)(=O)=[O:33].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:29][CH3:30])[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[CH:23]=[O:33])[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 570252831,1-Diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8ergolinyl]urea

Product 1

HCID 157465221,1-Diethyl-3-(6-methyl-2-formyl-8alpha-ergolinyl)ureaYield 61%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Under argon, 2.12 g (5 mmol) of 1,1-diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8ergolinyl]urea is dissolved in 40 ml of chloroform. Then 3.5 g of silica gel is added and, under vigorous agitation, 3.5 ml of water is introduced dropwise. During a time period of 30 minutes, a solution of 1.18 ml of sulfuryl chloride in 30 ml of chloroform is added dropwise. After 3 hours of agitation at room temperature, 7.5 g of potassium carbonate is added and the mixture vigorously stirred for 20 minutes. The precipitate is filtered off and rinsed with chloroform. The precipitate is moistened with ethanol and introduced into 300 ml of saturated sodium chloride solution which is then repeatedly extracted with chloroform. The chloroform extracts and the chloroform filtrate are dried together over magnesium sulfate and evaporated. Subsequent crystallization takes place from ethyl acetate, thus isolating 1.16 g of 1,1-diethyl-3-(6-methyl-2-formyl-8α-ergolinyl)urea (61% yield).

Workup

  1. additionis introduced dropwise
  2. filtrationThe precipitate is filtered off
  3. washrinsed with chloroform
  4. additionintroduced into 300 ml of saturated sodium chloride solution which
  5. extractionis then repeatedly extracted with chloroform
  6. dry with materialThe chloroform extracts and the chloroform filtrate are dried together over magnesium sulfate
  7. customevaporated
  8. customSubsequent crystallization

Sources & evidence

ORD record
ord-d3de9ca5b59b4728b0ca1f90a16f49ad
Source dataset
uspto-grants-1989_10
Patent number
US04874768

Reaction notes

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