HCID 140370881, compound → HCID 140370878, compound

HRID 487882Notes

Reaction equation

HRID 487882 reaction equation
[BrH:1].[C:2]([NH:5][C:6]([CH2:8][CH2:9][N:10]1[CH2:14][CH2:13]OC1=O)=[NH:7])(=[O:4])[NH2:3]>Br.C(O)(=O)C>[BrH:1].[BrH:1].[C:2]([NH:5][C:6]([CH2:8][CH2:9][NH:10][CH2:14][CH2:13][Br:1])=[NH:7])(=[O:4])[NH2:3]

Participants

4

Reactant 1

HCID 140370881HCID 140370881, compound

Product 1

HCID 140370878HCID 140370878, compoundYield 242.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 44 (20 g, 0.07 mol) in 200 mL of 30-32% HBr in acetic acid was vigorously stirred along with gradual heating (temperature up to 120° C.) over a period of 1 h. The mixture was cooled and filtered. The colorless crystals were washed with acetic acid (200 mL), ether (200 mL) and dried in vacuo overnight to give 22.6 g (80%) of 45: mp 170°-172° C. (dec) (note: Incomplete reaction will occur if the stirring is not efficient); 1H NMR (DMSO-d6) δ 3.05 [t, 2, --CH2 --C(N=)], 3.5 (b, 4, --CH2 --NH--CH2), 3.78, (t, 2, BrCH2 --).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe colorless crystals were washed with acetic acid (200 mL), ether (200 mL)
  4. customdried in vacuo overnight

Sources & evidence

ORD record
ord-c2f98c98d8bc4821ba28a27f46eb3322
Source dataset
uspto-grants-1994_03
Patent number
US05298499

Reaction notes

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