Sodium Azide → HCID 86609140, compound

HRID 902360Notes

Reaction equation

HRID 902360 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[C:17]([Cl:23])=[CH:18][CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:31]=[N+:32]=[N-:33].[Na+]>CS(C)=O>[N:31]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:17]([Cl:23])=[CH:18][CH:19]=2)[O:14]1)=[N+:32]=[N-:33]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609139HCID 86609139, compound

Product 1

HCID 86609140HCID 86609140, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Treatment of ((2R)-7-chloro-8-(2-chlorophenyl)chroman-2-yl)methyl 4-methylbenzenesulfonate (2.10 g, 4.53 mmol) with sodium azide (1.77 g, 27.20 mmol) in DMSO (50 mL) according to the procedure described for Example 69, Step 9 provided 1.5 g (99%) of (2R)-2-(azidomethyl)-7-chloro-8-(2-chlorophenyl)chroman as a white solid. MS (EI) m/z 333.0 [M]+.

Sources & evidence

ORD record
ord-c3bceb84018c4eb3a82d9a7dde66223e
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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