Water → HCID 178442323, compound

HRID 1160288Notes

Reaction equation

HRID 1160288 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

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59132658HCID 59132658, compound

Product 1

HCID 178442323HCID 178442323, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

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

Sources & evidence

ORD record
ord-42dcd378e1b841faa275759f71ff8d38
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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