Allyl bromide → HCID 21873363, compound

HRID 723361Notes

Reaction equation

HRID 723361 reaction equation
[H-].[K+].[CH2:3]([N:6]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)=[O:8])[CH:4]=[CH2:5].[CH2:37](Br)[CH:38]=[CH2:39]>C1COCC1.ClCCl>[CH2:39]([N:9]([C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][CH:15]=1)[C:7]([N:6]([CH2:3][CH:4]=[CH2:5])[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][CH:28]=1)=[O:8])[CH:38]=[CH2:37]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 82127Potassium hydrideHCID 21873324HCID 21873324, compound

Product 1

HCID 21873363HCID 21873363, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium hydride (30% in oil, 40 mg) was added to a solution of 1-allyl-1-(4-benzyloxyphenyl)-3-(4-phenoxyphenyl)urea (133 mg) in THF (3 mL) at −78° C. After 30 minutes, allyl bromide (30 μL) was added. After 14 hours at room temperature, the solution was diluted with dichloromethane and washed with saturated sodium bicarbonate solution. The organic phase was dried and concentrated. The product with the molecular weight of 490.61 (C32H30N2O3); MS (ESI): 491 ([M+H]+), was obtained in this way.

Workup

  1. waitAfter 14 hours at room temperature
  2. washwashed with saturated sodium bicarbonate solution
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customMS (ESI): 491 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-4aa67bc811bd45b88a69d51df4b33260
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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