Ethylene Glycol → HCID 69382402, compound

HRID 1351747Notes

Reaction equation

Cl.[CH2:2]([O:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([NH:18]N)[C:12]=1[CH3:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)CO.O.[O:27]1[CH:31]=[CH:30][CH2:29][CH2:28]1>CCOC(C)=O>[CH2:2]([O:9][C:10]([C:11]1[C:12]([CH3:20])=[C:13]2[C:14]([C:30]([CH2:29][CH2:28][OH:27])=[CH:31][NH:18]2)=[C:15]([Br:17])[CH:16]=1)=[O:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A 1000 mL RBF was charged with 5-bromo-3-hydrazino-2-methyl benzoic acid benzyl ester hydrochloride (30.0 g, 0.081 mol), ethylene glycol (350 mL), and water (60 mL). This mixture was heated to 40° C., and dihydrofuran (7.63 mL, 0.101 mol) was added. The reaction mixture was next heated to 100–105° C. with stirring for 2.25 hours. The reaction was then cooled to ambient temperature, diluted with EtOAc, washed with saturated NaCl (2×), dried (MgSO4), and concentrated. The resulting oil was chromatographed on SiO2, eluting with a 10% EtOAc/DCM to 50% EtOAc/DCM gradient. Isolation of the product as an impure solid, followed by trituration with DCM and hexanes, afforded 8.45 g (27.0%) of a pale yellow solid. 1H NMR (CDCl3) δ 8.28 (br s, 1 H), 7.94 (s, 1H), 7.40 (m, 6H), 5.36 (s, 2H), 3.96 (q, J=6.4 Hz, 2H), 3.28 (t, J=6.4 Hz, 2H), 2.72 (s, 3H).

Workup

temperatureThe reaction mixture was next heated to 100–105° C.
temperatureThe reaction was then cooled to ambient temperature
washwashed with saturated NaCl (2×)
dry with materialdried (MgSO4)
concentrationconcentrated
customThe resulting oil was chromatographed on SiO2
washeluting with a 10% EtOAc/DCM to 50% EtOAc/DCM gradient

Sources & evidence

ORD record: ord-1ffeb58ebdd445e19464ad4a7300bbfe
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217730B2

Reaction notes

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