Sodium Azide → HCID 11960763, compound

HRID 2116126Notes

Reaction equation

HRID 2116126 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C=CSC=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[S:31]1[CH:35]=[CH:34][C:33]([C:36]2[C:44]3[O:43][CH:42]([CH2:45][N:46]=[N+]=[N-])[CH2:41][C:40]=3[CH:39]=[CH:38][CH:37]=2)=[CH:32]1.[N-]=[N+]=[N-]>[Pd]>[S:31]1[CH:35]=[CH:34][C:33]([C:36]2[C:44]3[O:43][CH:42]([CH2:45][NH2:46])[CH2:41][C:40]=3[CH:39]=[CH:38][CH:37]=2)=[CH:32]1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599084HCID 86599084, compoundHCID 86599198HCID 86599198, compound

Product 1

HCID 11960763HCID 11960763, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (2.2 g, 5.64 mmol) with sodium azide (1.48 g, 22.77 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-(7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl azide. Treatment of the azide with palladium on carbon (0.130 g, 10 wt. %) generally according to the procedure described for Example 1 gave 0.838 g (55%) of (±)-1-(7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp >200° C.; Anal. calcd. for C13H13FNOSHCl: C, 58.31; H, 5.27; N, 5.23. Found: C, 56.4; H, 5.23; N, 4.95.

Sources & evidence

ORD record
ord-a2f5779046bc40d3b5be0fdd3c4c0e90
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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