Sodium Azide → HCID 61974743, compound

HRID 526271Notes

Reaction equation

HRID 526271 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]([CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:2][CH2:3][CH2:4][N:5]([CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 61975301N-(3-bromopropyl)-3-methoxy-N-methylaniline

Product 1

HCID 61974743HCID 61974743, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Compound 15 (0.5 g, 1.94 mmol) was dissolved in anhydrous DMF (20 mL) and sodium azide (1.26 g, 19.43 mmol) was added, followed by stirring of the reaction mixture at 70° C. for 16 hours. The remaining procedure was followed as described for compound 16 to obtain compound 17. Yield: 0.340 g (80%). 1H NMR (500 MHz, CDCl3): δ 1.86 (tt, 2H, J=6.5, 13.5 Hz, Hc), 2.93 (s, 3H, NCH3, Ha), 3.36 (t, 2H, J=6.5 Hz, Hd), 3.40 (t, 2H, J=7.5 Hz, Hb), 3.79 (s, 3H, OMe), 6.20-6.25 (m, 1H, Hi), 6.26-6.30 (m, 1H, Hg), 6.33-6.38 (m, 1H, He), 7.10-7.18 (m, 1H, Hf); 13C NMR (125 MHz, CDCl3): δ 26.32 (Cc), 38.56 (Ca), 49.14 (Cd), 49.77 (Cb), 55.10 (OCH3), 98.90 (Ci), 101.16 (Ce), 105.39 (Cg), 129.91 (Cf), 150.47 (Cj), 160.81 (Ch). EI-MS: [M+H]+ C11H17N4O calcd 221.14, obsd 221.12.

Sources & evidence

ORD record
ord-3977ee630ae84400b2c803671fcbda51
Source dataset
uspto-grants-2016_05
Patent number
US09345781B2

Reaction notes

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