Hydrogen Bromide → HCID 67128628, compound

HRID 2201722Notes

Reaction equation

HRID 2201722 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[CH:13][CH:12]=1)C1C=CC=CC=1.Br.C(OCC)C>C(O)(=O)C>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 67128715HCID 67128715, compound

Product 1

HCID 67128628HCID 67128628, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 3 (1.94 g, 0.005 mol) was stirred in 48% w/v hydrobromic acid in acetic acid (11 mL) for 1 h. Diethylether was added till a cream precipitate appeared and the ethereal solution decanted. The resulting white sticky solid was suspended in dichloromethane (100 mL) and 1 M aqueous sodium hydroxide (20 mL). The aqueous layer was extracted with dichloromethane (1×50 mL) and the combined organic layers were washed with saturated brine (1×50 mL), dried (MgSO4) and concentrated in vacuo to give 4 as a pale yellow oil (975 mg, 82%).

Workup

  1. customfor 1 h
  2. customthe ethereal solution decanted
  3. extractionThe aqueous layer was extracted with dichloromethane (1×50 mL)
  4. washthe combined organic layers were washed with saturated brine (1×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc70950476ef4c79b68938f48cfc337b
Source dataset
uspto-grants-2016_06
Patent number
US09365508B2

Reaction notes

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