Boron trifluoride etherate → HCID 13059863, compound

HRID 1721863Notes

Reaction equation

HRID 1721863 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[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][CH:13]=3)[N:9]([CH3:23])[CH2:8]1)=[O:5])[CH3:2].B(F)(F)F.CCOCC.S(Cl)([Cl:38])(=O)=O>C(#N)C.C(Cl)Cl>[Cl:38][C:13]1[NH:14][C:15]2[C:22]3[C:12]=1[CH2:11][C@@H:10]1[C@@H:20]([C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH2:21][C@@H:7]([NH:6][C:4](=[O:5])[N:3]([CH2:1][CH3:2])[CH2:24][CH3:25])[CH2:8][N:9]1[CH3:23]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 24648Sulfuryl chlorideHCID 57130390HCID 57130390, compound

Product 1

HCID 13059863HCID 13059863, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

In the same was as described in Example 7, 340 mg of 1,1-diethyl-3(6-methylergolinyl)urea (1 millimole) was dissolved in 19 ml of anhydrous acetonitrile and 0.3 ml of boron trifluoride etherate in 5 ml of anhydrous methylene chloride and reacted with 0.09 ml of freshly distilled sulfuryl chloride, dissolved in 10 ml of anhydrous methylene chloride. The product was worked up and chromatographed as described in Example 7, thus obtaining 270 mg of 3-(2-chloro-6-methyl-8β-ergolinyl)-1,1-diethylurea.

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-22188ada3f164fefbd03a2d492255c70
Source dataset
uspto-grants-1989_08
Patent number
US04853390

Reaction notes

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