Ammonium Chloride → HCID 59854635, compound

HRID 2112778Notes

Reaction equation

HRID 2112778 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16](Br)[C:15](=[O:27])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2].[Li+].[Br-].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[C:17]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:16]=[C:15]([OH:27])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 82050Lithium BromideHCID 59854724HCID 59854724, compound

Product 1

HCID 59854635HCID 59854635, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flame dried three-necked flask was purged with N2 and charged with bromide 01-5 (3.35 g, 7.4 mmol), LiBr (707 mg, 8.2 mmol, 1.1 equiv.), Li2CO3 (601 mg, 8.2 mmol, 1.1 equiv.) and DMF (85 mL). The resulting suspension was refluxed overnight under N2-atmosphere. The reaction mixture was cooled to RT and poured into saturated aqueous NH4Cl (500 mL). The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (3×200 mL), brine (200 mL) and dried over Na2SO4. The solvent was removed in vacuo to give the crude product as a brownish solid. The solid was washed with Et2O (25 mL) to give 01-6 (2.1 g, 5.7 mmol, 77%) as a slightly brown solid.

Workup

  1. customA flame dried three-necked flask was purged with N2
  2. temperatureThe resulting suspension was refluxed overnight under N2-atmosphere
  3. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  4. washThe combined organic layers were washed with H2O (3×200 mL), brine (200 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo
  7. customto give the crude product as a brownish solid
  8. washThe solid was washed with Et2O (25 mL)

Sources & evidence

ORD record
ord-80f3c0d848dc4401890ef8ee36cacb98
Source dataset
uspto-grants-2009_04
Patent number
US07524853B2

Reaction notes

Loading…