Ammonia → HCID 13823189, compound

HRID 649509Notes

Reaction equation

HRID 649509 reaction equation
[Br:1][C:2]1[C:16]2=[C:17]3[C:5]([NH:6][CH2:7][CH:8]3[CH2:9][C@@H:10]3[C@@H:15]2[CH2:14][C@H:13]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:12][N:11]3[CH3:26])=[CH:4][CH:3]=1.ClOC(C)(C)C.N>O1CCCC1.C(N(CC)CC)C>[Br:1][C:2]1[C:16]2=[C:17]3[C:5]([NH:6][CH:7]=[C:8]3[CH2:9][C@@H:10]3[C@@H:15]2[CH2:14][C@H:13]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:12][N:11]3[CH3:26])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 521297Tert-Butyl hypochloriteHCID 86742120HCID 86742120, compound

Product 1

HCID 13823189HCID 13823189, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 4.2 g of 3-(12-bromo-2,3-dihydro-6-methyl-8α-ergolinyl)-1,1-diethylurea in a mixture of 300 ml of absolute tetrahydrofuran and 50 ml of absolute triethylamine is combined at -40° C. with a solution of 1.58 ml of tert-butyl hypochlorite in 250 ml of absolute tetrahydrofuran, and the mixture is stirred for 15 minutes at -40° C. The reaction mixture is poured on 1 liter of ice, combined with 25% strength ammonia solution until the reaction is alkaline, and extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate and concentrated. The crude product is crystallized from ethyl acetate/pentane, thus obtaining 3 g of 3-(12-bromo-6-methyl-8α-ergolinyl)-1,1-diethylurea.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product is crystallized from ethyl acetate/pentane

Sources & evidence

ORD record
ord-bd13f7066a4e4fdfa7ddc3971626ac18
Source dataset
uspto-grants-1988_04
Patent number
US04740509

Reaction notes

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