Water → 5-[4-(benzyloxy)2-methoxyphenyl]-2H-tetrazole

HRID 22827

Reaction equation

HRID 22827 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+].Cl.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]2[N:19]=[N:20][NH:21][N:14]=2)=[C:11]([O:17][CH3:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 225917204-(Benzyloxy)-2-methoxybenzonitrile

Product 1

HCID 225917185-[4-(benzyloxy)2-methoxyphenyl]-2H-tetrazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A vigorously stirred suspension of 4-benzyloxy-2-methoxybenzonitrile (1-B) (1.20 g, 5.0 mmol), sodium azide (732 mg, 11.3 mmol), and triethylamine hydrochloride (1.54 g, 11.3 mmol) in toluene (6 mL) was heated at 110° for 48 h. The brown suspension was cooled, water (15 mL) was added, and the mixture stirred for 30 min. The organic layer was separated and extracted with water (5 mL). The combined aqueous extracts were acidified to about pH 1 with concentrated HCl. The gum that initially precipitated solidified upon stirring for 30 min. The solid was filtered, washed with water, and dried to give 5-[4-(benzyloxy)2-methoxyphenyl]-2H-tetrazole (1-C). 1H NMR (500 MHz, CDCl3): δ 12.9 (vbs, 1H), 7.37 (d, 1H, J=8.7 Hz), 7.34-7.48 (m, 5H), 6.78 (dd, 1H, J=2.3, 8.7 Hz), 6.70 (d, 1H, J=2.3 Hz), 5.15 (s, 2H), 4.05 (s, 3H) ppm.

Workup

  1. temperaturewas heated at 110° for 48 h
  2. temperatureThe brown suspension was cooled
  3. customThe organic layer was separated
  4. extractionextracted with water (5 mL)
  5. customThe gum that initially precipitated
  6. stirringupon stirring for 30 min
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-d7f602c1d4704f5585847a823c360e27
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Linked notes

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