N-bromobutanimide → HCID 15703643, compound

HRID 2351277Notes

Reaction equation

HRID 2351277 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][Br:19])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19845686HCID 19845686, compound

Product 1

HCID 15703643HCID 15703643, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of ethyl 2-ethoxycarbonylamino-6-methylbenzoate (10 mmol, 2.513 g.), N-bromosuccinimide (11 mmol, 1.957 g.), and catalytic amount (100 mg) of AIBN (2,2'-azobisisobutyronitrile) in 50 ml carbon tetrachloride was refluxed for 2 hours. The insoluble succinimide was removed by filtration. The filtrate was washed with saturated NaHCO3 solution (25 ml), water (30 ml), dried over MgSO4, and filtered. The filtrate was evaporated to dryness and trituated with petroleum ether to afford 2.44 g (74%) of ethyl 2-ethoxycarbonylamino-6-bromomethylbenzoate (6) as a pale yellow powder; mp 70°-72° C. IR (KBr) νmax 1740, 1685 cm-1.

Workup

  1. customThe insoluble succinimide was removed by filtration
  2. washThe filtrate was washed with saturated NaHCO3 solution (25 ml), water (30 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-47dbaf86c4da4b43ae6f115dc0f80869
Source dataset
uspto-grants-1989_10
Patent number
US04873232

Reaction notes

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