Water → HCID 178442323, compound

HRID 1993037Notes

Reaction equation

[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]#[C:17][CH3:18])[CH2:13][C:14]#[N:15])=[CH:8][CH:7]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].O>CN(C=O)C>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]#[C:17][CH3:18])[CH2:13][C:14]2[NH:25][N:24]=[N:23][N:15]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 23.3 (200 mg, 0.51 mmol) in DMF (5 mL) was added sodium azide (35 mg, 0.54 mmol) and ammonium chloride (29 mg, 0.54 mmol). The solution was stirred at 110° C. for 48 hours. The reaction mixture was poured into 50 mL of water and extracted with ethyl acetate (2×25 mL). The combined organic layers were concentrated under reduce pressure, and the resulting residue was purified via HPLC to yield 5 mg (3%) of 5-{2-[4-(2-Methyl-benzyloxy)-phenyl]-pent-3-ynyl}-1H-tetrazole (23) as a film. LC/MSD m/e: 333.1 (M+H). 1H NMR (400 MHz) (acetone-d6) δ 7.45 (1H, m), 7.34 (2H, m), 7.25 (3H, m), 7.00 (2H, m), 5.11 (2H, s), 4.17 (1H, m), 3.37 (2H, d, J=7 Hz), 2.39 (3H, s), 1.79 (3H, s).

Workup

extractionextracted with ethyl acetate (2×25 mL)
concentrationThe combined organic layers were concentrated
customthe resulting residue was purified via HPLC

Sources & evidence

ORD record: ord-c187e62138b741a9a1b7440f51e4ee2b
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649110B2

Reaction notes

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