Bromoacetyl bromide → 1-Vinyl pyrrolidone bromoacetate

HRID 2292996

Reaction equation

HRID 2292996 reaction equation
[CH:1]([N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])=[CH2:2].C([OH:11])=C.[Br:12][CH2:13][C:14](Br)=[O:15]>CN(C)C=O>[CH:1]([N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])=[CH2:2].[Br:12][CH2:13][C:14]([O-:15])=[O:11]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 3082248poly(vinyl alcohol-co-N-vinyl-2-pyrrolidone)

Product 1

HCID 867515071-Vinyl pyrrolidone bromoacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution containing 330 mg of 1-vinyl pyrrolidone/vinyl alcohol copolymer (VI) in 8 mL of dry dimethyl formamide was taken in a two-neck round-bottomed flask and connected to nitrogen. The other neck was capped with a septum stopper. The flask was cooled in an ice bath. To the flask 0.25 mL of bromoacetyl bromide dissolved in 2 mL of DMF was added dropwise with a syringe through the septum stopper. The reaction was allowed to proceed at room temperature for 1 hour in the dark. The precipitation of the reaction mixture in 15-fold diethyl ether for 5 times yielded 270 mg of 1-vinyl pyrrolidone/bromoacetate copolymer (VII). A test of alkylating agents using 4-(p-nitrobenzyl)pyridine was positive indicating the presence of alkyl bromide in the copolymer (5). C-13 NMR (CD3OD) : 19.2, 27.4, 32.5, 33.7-37.1, 43.6-45.5, 48.2-48.9, 70.0-71.5, 168.6, 177.7. Elemental Analysis: found (Calcd): C, 40.05 (43.5); H, 4.87 (5.11); Br, 30.97 (28.94); N, 5.43 (5.07).

Workup

  1. customwas taken in a two-neck round-bottomed flask
  2. customThe other neck was capped with a septum stopper
  3. temperatureThe flask was cooled in an ice bath
  4. additionwas added dropwise with a syringe through the septum stopper
  5. customThe precipitation of the reaction mixture in 15-fold diethyl ether for 5 times

Sources & evidence

ORD record
ord-bc74b0b4c8e54728a853463be0e53f76
Source dataset
uspto-grants-1997_11
Patent number
US05686071

Linked notes

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