Ethyl bromoacetate → HCID 13339962, compound

HRID 647874Notes

Reaction equation

HRID 647874 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:7]=2[NH:6][C:5]1=[O:17])=[N+:2]=[N-:3].[OH-].[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:7]=2[N:6]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:5]1=[O:17])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 13243505HCID 13243505, compound

Product 1

HCID 13339962HCID 13339962, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Azido-8-methoxy-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (5 g) was added in one portion to a stirred suspension of potassium hydroxide (1.3 g) and tetrabutylammonium bromide (0.7 g) in tetrahydrofuran (50 ml) maintained at 0° under a nitrogen atmosphere. Stirring was continued for 5 minutes, then a solution of ethyl bromoacetate (3.6 g) in tetrahydrofuran (15 ml) was added during 5 minutes. The reaction mixture was allowed to warm to room temperature while stirring for an additional 2 hours. The reaction mixture was filtered and the tetrahydrofuran was removed at reduced pressure. The residue was partitioned between water (50 ml) and ether (100 ml). The organic phase was washed with 2N hydrochloric acid (10 ml), dried over magnesium sulfate and the solvent removed under reduced pressure to give 3-azido-1-ethoxycarbonylmethyl-8-methoxy-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one, m.p. 90°-91°.

Workup

  1. temperaturemaintained at 0° under a nitrogen atmosphere
  2. stirringwhile stirring for an additional 2 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe tetrahydrofuran was removed at reduced pressure
  5. customThe residue was partitioned between water (50 ml) and ether (100 ml)
  6. washThe organic phase was washed with 2N hydrochloric acid (10 ml)
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c5924801350e4a5f9c278917804db7f4
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

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