Bromoacetyl bromide → HCID 18929204, compound

HRID 1599828Notes

Reaction equation

HRID 1599828 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[Br:11][CH2:12][C:13](Br)=[O:14]>CN(C=O)C.O1CCOCC1.O>[Br:11][CH2:12][C:13]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1)=[O:14]

Participants

6

Reactant 2

HCID 61147Bromoacetyl bromideHCID 770004-Aminophenylacetonitrile

Product 1

HCID 18929204HCID 18929204, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-aminobenzyl cyanide (4 g, 0.03 mol) in anhydrous DMF (20 mL) and anhydrous dioxane (20 mL) in a 3-necked flask, fitted with magnetic stirrer and a constant additional funnel, was added, dropwise, bromoacetyl bromide (6.12 g, 2.7 mL, 100 mol %) while keeping the internal temperature between 0° C. and 2° C. After the addition was completed (~25 min), the reaction mixture was stirred overnight at rt. The reaction mixture was diluted with water (100 mL) and then the yellow crystalline compound which precipitated was filtered, washed sequentially with 5% HBr (100 mL) and water (200 mL), and then dried in a vacuum oven at 40°-45° C., affording 5.0 g (66%) of the title compound: mp 129°-131° C.; 1H NMR (DMSO-d6) δ10.46 (s, 1H , NH), 7.60 (d, 2H, J=8.4), 7.31 (d, 2H, J=8.8), 4.04 (s, 2H), 3.98 (s, 2H): 13C NMR (DMSO-d6) δ164.82; 137.99; 128.60; 126.42; 119.61; 30.30; 21.82; MS (EI, m/z) 252 (M+). HRMS (EI) calcd for C10H9N2OBr 251.9898, found 251.9882.

Workup

  1. additionwas added
  2. customthe internal temperature between 0° C. and 2° C
  3. additionAfter the addition
  4. custom(~25 min)
  5. customthe yellow crystalline compound which precipitated
  6. filtrationwas filtered
  7. washwashed sequentially with 5% HBr (100 mL) and water (200 mL)
  8. customdried in a vacuum oven at 40°-45° C.

Sources & evidence

ORD record
ord-bb67244b60794100a87434c36fdd0373
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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