Ammonium Chloride → HCID 178421934, compound

HRID 731031Notes

Reaction equation

HRID 731031 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:20]=[CH:19][C:14]([O:15][CH2:16][C:17]#[N:18])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH3:21])=[C:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:20]=[CH:19][C:14]([O:15][CH2:16][C:17]4[NH:30][N:29]=[N:28][N:18]=4)=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH3:21])=[C:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68815118HCID 68815118, compound

Product 1

HCID 178421934HCID 178421934, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 6 of example 3. Thus, [4-(1,3-dimethyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.355 g, 1.007 mmol) was reacted with NaN3 (0.327 g, 5.036 mmol) and NH4Cl (0.269 g, 5.036 mmol) in DMF (5 ml) to give the desired product (0.302 g, 0.764 mmol, 76%) as a white solid, dec. 261-262° C. 1H NMR (DMSO-d6) δ 2.25 (s, 3H), 3.61 (s, 3H), 5.52 (s, 2H), 7.14 (d, J=8.6 Hz, 2H), 7.45-7.51 (m, 5H), 7.55 (t, J=7.6 Hz, 2H), 7.67 (d, J=8.6 Hz, 2H), 7.75 (s, 1H), 16.80 (broad s, 1H); IR (solid) 3040, 2860, 2620, 1580, 1520, 1480, and 1230 cm−1; [ESI(+)], m/z 396 (M+H)+; Anal. Calcd. for C24H21N5O: C, 72.89; H, 5.35; N, 17.71; Found: C, 72.84; H, 5.33; N, 17.80.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-4b5d822b456e442e8562ca39c65bfa7a
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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