Water → HCID 69691057, compound

HRID 394780Notes

Reaction equation

HRID 394780 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Br[CH2:11][C:12](OCC)=O.[C:17](=[O:20])([O-])[O-:18].[Na+].[Na+].O.[CH3:24]N(C=O)C>>[CH2:11]([N:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:24][C:17]([OH:18])=[O:20])[CH3:12]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7732P-AnisidineHCID 7748Ethyl bromoacetateHCID 10340Sodium Carbonate

Product 1

HCID 69691057HCID 69691057, compoundYield 88%

Conditions

Temperature
70 °C

Procedure

To a solution of 15.00 g (122 mmol) of p-anisidine in 100 mL of DMF under N2 was added 23.50 g (141 mmol) of ethyl bromoacetate and 14.95 g (141 mmol) anhydrous sodium carbonate. The mixture was heated to 70° C. for 16 hours and then cooled to room temperature. Water (500 mL) was added and the mixture stirred vigorously until a precipitate formed. The solid was collected and washed with 100 mL water, then dried in vacuo to give 19.59 g (88%) of the desired compound as a grey solid. 1H NMR (CDCl3): δ 6.81 (d, J=8.8, 2H); 6.579 (d, J=8.8, 2H); 4.24 (q, J=7.0, 2H); 4.10 (s, 1H); 3.86 (s, 2H); 3.75 (s, 3H); 1.28 (t, J=7.0, 3H).

Workup

  1. temperaturecooled to room temperature
  2. customformed
  3. customThe solid was collected
  4. washwashed with 100 mL water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ac03dd621a0a4ac7b7daf9b81cd1d111
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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