Ammonium Chloride → 2,4-dibromo-N-(4-(tert-butoxycarbonylamino)phenyl)-butyramide

HRID 2299013Notes

Reaction equation

HRID 2299013 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][Br:8])[C:3](Br)=[O:4].[C:9]([O:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[NH4+].[Cl-]>ClCCl>[Br:1][CH:2]([CH2:6][CH2:7][Br:8])[C:3]([NH:23][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])=[CH:22][CH:21]=1)=[O:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 112898262,4-dibromobutanoyl Bromide

Product 1

HCID 183794652,4-dibromo-N-(4-(tert-butoxycarbonylamino)phenyl)-butyramideYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the derivative 2,4-dibromobutyryl bromide (3.1 g) in dry dichloromethane (60 ml) pyridine (3.2 ml was added, the mixture was kept at 0° C. under a nitrogen atmosphere for 10 minutes and then the N-t-butoxy carbonyl-1,4 phenylene diamine (2.08 g) was dropped. After 1 hour the mixture was poured into a saturated solution of NH4Cl (200 ml) extracted with EA (3×150 ml) and the organic phase washed with brine (200 ml), dried and concentrated in vacuum, the crude was purified by flash chromatography (eluting with CH/EA 80:20) to give of the title compound as a yellow foam (3.5 g ). T.I.c. CH/EA 8:2, Rf=0.53.

Workup

  1. extractionextracted with EA (3×150 ml)
  2. washthe organic phase washed with brine (200 ml)
  3. customdried
  4. concentrationconcentrated in vacuum
  5. customthe crude was purified by flash chromatography (eluting with CH/EA 80:20)

Sources & evidence

ORD record
ord-6d9ee3a931c64a5c9a19d0837331b76d
Source dataset
uspto-grants-2002_12
Patent number
US06495566B2

Reaction notes

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