Sodium Azide → (+/-)-[4-(2,6-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide

HRID 2116188Notes

Reaction equation

HRID 2116188 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[C:18]([C:22]4[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:29])=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+]>>[CH3:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([CH3:28])[C:22]=1[C:18]1[C:16]2[CH2:17][CH:13]([CH2:12][N:30]=[N+:31]=[N-:32])[O:14][C:15]=2[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 86599131(+/-)-[4-(2,6-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 86599241(+/-)-[4-(2,6-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azideYield 91%

Procedure

Treatment of (±)-[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (2.27 g, 5.55 mmol) with sodium azide (1.44 g, 22.23 mmol) generally according to the procedure described for Intermediate 98 gave 1.41 g (91%) of (±)-[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide. Treatment of the azide with palladium on carbon (0.141 g, 10 wt. %) generally according to the procedure described for Example 1 provided 1.36 g (93%) of (±)-1-[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 254-256° C.; Anal. calcd. for C17H19NOHCl: C, 70.46; H, 6.96; N, 4.83. Found: C, 69.03; H, 7.05; N, 4.66.

Sources & evidence

ORD record
ord-b38dd8336e6e44c98f859c02ae742380
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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