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

HRID 569331Notes

Reaction equation

HRID 569331 reaction equation
[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]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 867420541,1-Diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]urea

Product 1

HCID 157465221,1-Diethyl-3-(6-methyl-2-formyl-8alpha-ergolinyl)ureaYield 54%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.05 g (5 mmol) of 1,1-diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8α-ergolinyl]urea is dissolved under argon in 46 ml of chloroform. Then 3.5 g of silica gel and, under vigorous agitation, dropwise 3.5 ml of water are added. During a time period of 30 minutes, a solution of 1.18 ml of sulfuryl chloride in 30 ml of chloroform is added drop by drop. After stirring for 3 hours at room temperature, 7.5 g of potassium carbonate is added and the mixture is vigorously stirred for 20 minutes. The precipitate is filtered off and washed 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 jointly dried over magnesium sulfate and evaporated. The subsequent crystallization is performed from ethyl acetate, thus isolating 0.93 g of 1,1-diethyl-3-(6-methyl-2-formyl-8α-ergolinyl)urea (54% yield).

Workup

  1. stirringthe mixture is vigorously stirred for 20 minutes
  2. filtrationThe precipitate is filtered off
  3. washwashed 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 jointly dried over magnesium sulfate
  7. customevaporated
  8. customThe subsequent crystallization

Sources & evidence

ORD record
ord-0e45f6c78f26450e837ddd345fc81e61
Source dataset
uspto-grants-1988_03
Patent number
US04731367

Reaction notes

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