N-bromobutanimide → HCID 67451842, compound

HRID 1519231Notes

Reaction equation

HRID 1519231 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][O:17][CH2:16][CH2:15]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)Cl>[Br:27][C:10]1[N:11]=[C:12]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[O:13][C:9]=1[S:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67452000HCID 67452000, compound

Product 1

HCID 67451842HCID 67451842, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (5.21 g, 17.61 mmol) in DCM (176 ml) was added NBS (3.45 g, 19.38 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, 5 to 30% EtOAc in hexane), to give 4-bromo-5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (6.16 g). MS: M+H=376. H1NMR (400 MHz, CDCl3) δ: 7.28 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 4.01 (dt, J=11.7 Hz, 3.6 Hz, 2H), 3.50 (td, J=11.7 Hz, 2.7 Hz, 2H), 3.09-2.98 (m, 1H), 2.02-1.86 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica 330 g, 5 to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-7c7a996afd7c420ab44aefc80233a6e8
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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