Chloride → HCID 18929198, compound

HRID 1599841Notes

Reaction equation

HRID 1599841 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.CN(C=O)C.[Br:17][CH2:18][C:19](Br)=[O:20].[Cl-]>O1CCOCC1>[Br:17][CH2:18][C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)=[O:20]

Participants

6

Reactant 4

HCID 312ChlorideHCID 6228DimethylformamideHCID 145334-Aminophenylacetic acidHCID 61147Bromoacetyl bromide

Product 1

HCID 18929198HCID 18929198, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-aminophenylacetic acid (3.0 g, 19.8 mmol) in a mixture of anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) in a 250 mL 3-necked round-bottomed flask equipped with a constant addition funnel (60 mL) was cooled to 0° C. using an ice-bath. Bromoacetyl bromide (4.00 g, 1.74 mL, 19.8 mmol) was added dropwise, keeping the internal temperature between 0° and 5° C. over a 1/2 h period. After the addition of the chloride was completed, the solution was warmed to rt, stirred overnight, and then the solution was slowly poured into 500 mL of ice-water. The resulting precipitate was filtered, washed with water, add then dried in a vacuum dessicator overnight to afford 2.75 (51%) of the title compound as a pale yellow crystals, mp 168°-171° C.: 1H NMR (DMSO-d6) δ12.28 (bs, 1H), 10.36 (s, 1H), 7.50 (d, J=8.8, 2H), 7.20 (d, J=8.4, 2H), 4.02 (s, 2H), 3.51(s, 2H); 13C NMR (DMSO-d6) δ172.70, 164.65, 137.12, 130.45, 129.76, 119.12, 40.12, 30.40; MS (EI, m/z) 271 (M+).

Workup

  1. customequipped with a constant addition funnel (60 mL)
  2. customthe internal temperature between 0° and 5° C.
  3. customover a 1/2 h
  4. temperaturethe solution was warmed to rt
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. additionadd
  8. customthen dried in a vacuum dessicator overnight

Sources & evidence

ORD record
ord-799085e330b84f0ea5be14f683b1cdc8
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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