Hydrochloric Acid → HCID 54328878, compound

HRID 1464273Notes

Reaction equation

HRID 1464273 reaction equation
O=[C:2]1O[C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[NH:3]1.[H-].[Na+].BrC/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20].[OH-].[NH4+:25].Cl>CN(C)C=O>[CH2:22]([O:21][C:19]([CH:18]=[CH:17][CH2:2][NH:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:25])=[O:8])=[O:20])[CH3:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 14923Ammonium HydroxideHCID 24758Sodium hydrideHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 54328878HCID 54328878, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,4-dioxo-1H-3,1-benzoxazine (2.00 g) in dry dimethylformamide (20 ml) was added sodium hydride (540 mg, 60% oil suspension) in several portions on an ice-bath. After 30 minutes, ethyl 4-bromocrotonate (3.79 g) was added to the mixture. After stirring for additional 2 hours at room temperature, 28% ammonium hydroxide (7.5 ml) was added on an ice-bath. The mixture was stirred for 30 minutes at the same temperature, neutralized with 1N hydrochloric acid, extracted with ethyl acetate. Combined organic extract was washed in turn with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (120 g) eluting with ethyl acetate and hexane (1:1 V/V) to give 2-(3-ethoxycarbonyl-2-propenylamino)benzamide (2.53 g) as a solid.

Workup

  1. stirringThe mixture was stirred for 30 minutes at the same temperature
  2. extractionextracted with ethyl acetate
  3. extractionCombined organic extract
  4. washwas washed in turn with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (120 g)
  8. washeluting with ethyl acetate and hexane (1:1 V/V)

Sources & evidence

ORD record
ord-d4bf972f04af4f14b85c4bdd10a5c132
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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