Hydrogen Bromide → HCID 10198785, compound

HRID 1250269Notes

Reaction equation

HRID 1250269 reaction equation
[CH3:1][N:2](C(OC(C)(C)C)=O)[CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:9]=1)[CH3:4].Br>>[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:9]=1)[CH3:4]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 18327736HCID 18327736, compound

Product 1

HCID 10198785HCID 10198785, compoundYield 99.8%

Conditions

Temperature
0 °C

Procedure

A solution of (4E)-N-methyl-N-(tert-butoxycarbonyl)-5-(3-acetamido-4-methylphenyl)-4-penten-2-amine (0.90 g, 2.60 mmol) and aqueous hydrobromic acid (50%, 25 mL) was stirred at 0° C. to ambient temperature for ˜16 h. The reaction mixture was extracted with chloroform (40 mL). The aqueous layer was cooled to 0° C., basified with aqueous sodium hydroxide solution to pH 8-9, and extracted with chloroform (4×50 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator to yield 0.639 g (94.6%) of a colorless oil.

Workup

  1. extractionThe reaction mixture was extracted with chloroform (40 mL)
  2. extractionextracted with chloroform (4×50 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-af96af9ae0eb4e669f03283ce09a8212
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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