N-bromobutanimide → N-(3-(5-bromothiophen-2-ylthio)propyl)acetamide

HRID 1484932Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C>[Br:21][C:5]1[S:1][C:2]([S:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of N-(3-(thiophen-2-ylthio)propyl)acetamide (2.5 g, 11.6 mmol, 1.0 eq), NBS (2.1 g, 11.6 mmol, 1.0 eq) in DMF (5 mL) was stirred at 23° C. for 1 hour. The mixture was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated to give yellow oil N-(3-(5-bromothiophen-2-ylthio)propyl)acetamide (1.6 g, 46.8%);

Workup

extractionThe mixture was extracted with CH2Cl2
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-88c9a294fb1641bba8c26173ec370256
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

Loading…