N-bromobutanimide → HCID 67452095, compound

HRID 716717Notes

Reaction equation

HRID 716717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([CH:14]3[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][CH2:15]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:31])C(=O)C1>C(Cl)Cl>[Br:31][C:10]1[N:11]=[C:12]([CH:14]2[CH2:15][CH2:16][CH:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:19]2)[O:13][C:9]=1[S:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67454279HCID 67454279, compound

Product 1

HCID 67452095HCID 67452095, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-{5-[(4-chlorophenyl)sulfanyl]-1,3-oxazol-2-yl}cyclohexanecarboxylate (3.762 g, 10.69 mmol) in DCM (107 ml) was added NBS (2.093 g, 11.76 mmol) and the reaction mixture was stirred at RT for 16 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica 330 g, 0 to 25% EtOAc in hexane), to give methyl 4-{4-bromo-5-[(4-chlorophenyl)sulfanyl]-1,3-oxazol-2-yl}cyclohexanecarboxylate (3.5 g), as a ca. 2:1 mixture of trans/cis isomers. LCMS: M+H 430.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica 330 g, 0 to 25% EtOAc in hexane)

Sources & evidence

ORD record
ord-5991cf5f4d464faea16f9303187352b3
Source dataset
uspto-grants-2015_11
Patent number
US09193697B2

Reaction notes

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