N-bromobutanimide → Methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

HRID 1710782Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[Br:22]N1C(=O)CCC1=O>C(#N)C>[Br:22][C:7]1[CH:8]=[C:9]([C:12]2[S:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][Cl:1]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate ax60 (2 g, 6.15 mmol, 1 eq) in acetonitrile (50 ml) is treated with a solution of N-bromosuccinimide (1.8 g, 10 mmol, 1.5 eq) in acetonitrile (10 ml) and the resulting solution is stirred 2 h at room temperature and 2 h at 60° C. After cooling, the mixture is concentrated to dryness. The residue is taken up with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Purification of the residue over silicagel (eluent: dichloromethane/benzine) affords 0.6 g of methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i91.

Workup

temperatureAfter cooling
concentrationthe mixture is concentrated to dryness
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customPurification of the residue over silicagel (eluent: dichloromethane/benzine)

Sources & evidence

ORD record: ord-c1f7d4a7954c4507ac4cf1102712b33f
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790720B2

Reaction notes

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