Ethyl bromoacetate → HCID 20098261, compound

HRID 1768915Notes

Reaction equation

HRID 1768915 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][C:9]1[NH:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1.C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[NH2:8][C:9]1[N:13]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:10]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 6165951H-Imidazol-2-amine, 4,5-diphenyl-

Product 1

HCID 20098261HCID 20098261, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl bromoacetate (3.50 mL, 31.87 mmol) was added to a solution of 2-amino-4,5-diphenylimidazole (7.50 g, 31.87 mmol) and 1,8-diazobicyclo[5.4.0]undec-7-ene (4.80 mL, 31.87 mmol) in anhydrous tetrahydrofuran (150 mL). The mixture was heated to about 75° C. for about 2 hours and at about 65° C. for about 16 hours before it was cooled to room temperature and treated with brine. After about 15 minutes, ethyl acetate was added and the organic phase was separated, washed with saturated sodium bicarbonate solution and brine prior to drying and solvent concentration to one quarter volume. The precipitate which formed on concentration of the solvent was collected by suction-filtration. There was isolated 3.67 g (36%) of the title compound as an off-white solid. An additional 2.56 g (25%) of the title compound was isolated from the filtrate on concentration, m.p. 173°-175° C.; 1H NMR (CD3SOCD3) δ 7.46-7.36 (m, 3H), 7.32-7.29 (m, 2H), 7.25-7.21 (m, 2H), 7.17-7.04 (m, 2H), 7.03-6.99 (m, 1H), 5.78 (s, 2H), 4.36 (s, 2H), 4.03 (q, J=7.1 Hz, 2H), 1.08 (t, J=7.1 Hz, 3H); 13C NMR (CD3SOCD3) ppm 170.07, 151.51, 137.08, 133.74, 133.02, 132.50, 130.74, 130.01, 129.59, 128.55, 127.26, 127.06, 124.83, 62.62, 45.71, 15.69; IR (KBr, cm-1) 3410, 3390, 3062, 2980, 1744, 1660, 1562, 1476, 1340, 1240, 1222, 1212, 1026, 772, 700; MS m/z (MH+) calcd 322.1556, obsd 322.1555.

Workup

  1. temperaturewas cooled to room temperature
  2. customthe organic phase was separated
  3. washwashed with saturated sodium bicarbonate solution and brine
  4. customto drying
  5. concentrationsolvent concentration to one quarter volume
  6. customThe precipitate which formed on concentration of the solvent
  7. filtrationwas collected by suction-filtration

Sources & evidence

ORD record
ord-57a3cd8dff934be0a4e646c682ccf959
Source dataset
uspto-grants-1995_01
Patent number
US05380713

Reaction notes

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