Sodium Azide → HCID 86599187, compound

HRID 2116114Notes

Reaction equation

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

Participants

Reactant 2

HCID 33557Sodium Azide

HCID 86599062HCID 86599062, compound

Product 1

HCID 86599187HCID 86599187, compound

Procedure

Treatment of (±)-(6-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (0.280 g, 0.736 mmol) with sodium azide (0.191 g, 2.94 mmol) generally according to the procedure described for Intermediate 98 gave (±)-(6-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide. Treatment of the azide with palladium on carbon (0.026 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.190 g (90%) of (±)-(6-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a tan solid, hydrobromide salt. mp 218-221° C. Anal. calcd. for C15H15NOHBr: C, 58.84; H, 5.27; N, 4.57. Found: C, 54.80; H, 4.88; N, 4.18.

Sources & evidence

ORD record: ord-bebccbd175924286a580bc1695553984
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

Loading…