Ammonium Chloride → HCID 59854635, compound

HRID 2112783Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][C:16](CC3C=CC=CC=3)(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]([CH2:6][C:7]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:8]=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

Conditions

Temperature: 150 °C

Procedure

A suspension of the bromide 02-5 (8.5 g, 18.9 mmol), LiBr (1.8 g, 20.8 mmol, 1.1 equiv.), Li2CO3 (1.5 g, 20.8 mmol, 1.1 equiv.) and DMF (200 mL) was heated to 150° C. for 4 h under a N2-atmosphere. The reaction mixture was cooled to RT and poured into saturated aqueous NH4Cl (750 mL). The aqueous layer was extracted with EtOAc (3×200 mL). The combined organic layers were washed with H2O (3×200 mL), sat. aq. NH4Cl (200 mL) and dried over Na2SO4. The solvent was removed in vacuo to give the crude product. The solid was washed with Et2O (25 mL) to give 02-6 (1.52 g, 4.1 mmol, 22%). The filtrate was evaporated and the residue was purified by column chromatography (SiO2, EtOAc/hept=1/1) to give another fraction of 02-6 (2.5 g, 6.8 mmol, 36%) as a yellow solid (total yield: 4.3 g, 11.7 mmol, 62%).

Workup

temperatureThe reaction mixture was cooled to RT
extractionThe aqueous layer was extracted with EtOAc (3×200 mL)
washThe combined organic layers were washed with H2O (3×200 mL), sat. aq. NH4Cl (200 mL)
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo
customto give the crude product
washThe solid was washed with Et2O (25 mL)

Sources & evidence

ORD record: ord-121086e85a7544ba99c4a7371690acce
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524853B2

Reaction notes

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