Hydrogen Bromide → HCID 178419258, compound

HRID 487880Notes

Reaction equation

HRID 487880 reaction equation
Cl.[CH3:2][NH:3][C:4]([CH2:6][CH2:7][N:8]1[CH2:12][CH2:11]OC1=O)=[NH:5].[BrH:14]>CC(O)=O>[BrH:14].[BrH:14].[CH3:2][NH:3][C:4]([CH2:6][CH2:7][NH:8][CH2:12][CH2:11][Br:14])=[NH:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178484970HCID 178484970, compound

Product 1

HCID 178419258HCID 178419258, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 19 (10 g, 0.048 mol) was added in portions to a well stirred saturated solution of 100 mL of HBr in AcOH at room temperature. After addition, the mixture was stirred overnight, the precipitated solid was separated by filtration, washed with ether (200 mL) and dried in vacuo over KOH. Recrystallization from methanol-ether afforded 14.2 g (80%) of 20 as colorless crystals: mp 155° C. (dec); 1H NMR (CD3OD) δ 2.96 (s, 3, NCH3), 3.05 [t, 2, CH2CH2 (NH)], 3.49-3.64 (m, 4, CH2N--CH2) and 3.8 (t, 2, CH2CH2Br).

Workup

  1. additionAfter addition
  2. customthe precipitated solid was separated by filtration
  3. washwashed with ether (200 mL)
  4. dry with materialdried in vacuo over KOH
  5. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-5cbdd83554f640ae86db83c24253e205
Source dataset
uspto-grants-1994_03
Patent number
US05298499

Reaction notes

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