Sodium Azide → [4-(4-Azidobutyl)phenyl]acetic acid
Reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14]OS(C)(=O)=O)=[CH:7][CH:6]=1)([OH:3])=[O:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][N:20]=[N+:21]=[N-:22])=[CH:7][CH:6]=1)([OH:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Compound 6 (6 g, 0.02 mol) was dissolved in 80 ml of dry DMF then sodium azide (1.8 g, 0.027 mol) was added. The suspension was stirred at 80° C. (oil bath) for 3 h. The solvent was then removed at reduced pressure and the residual oil was treated with CH2Cl2 (100 mL). The resulting solution was washed with water (2×100 mL), brine and dried over magnesium sulfate. The solvent was removed under reduced pressure then the residue was redissolved in a 1:1 mixture of ethyl acetate/hexanes (200 mL) and passed through a pad of silica gel. The solvent was removed under reduced pressure to give 4.1 g (85%) of 7 as clear oil. 1H NMR (300 MHz, CDCl3) δ 1.68 (m, 4H), 2.22 (t, 2H), 3.29 (t, 3H), 3.92 (s, 3H), 7.28 (d, 2H) 7.98 (d, 2H).
Workup
- customThe solvent was then removed at reduced pressure
- additionthe residual oil was treated with CH2Cl2 (100 mL)
- washThe resulting solution was washed with water (2×100 mL), brine
- dry with materialdried over magnesium sulfate
- customThe solvent was removed under reduced pressure
- dissolutionthe residue was redissolved in a 1:1 mixture of ethyl acetate/hexanes (200 mL)
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-0215e65b676e4b188998d04e38781d4c
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858615B2
Reaction notes
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