Ammonium Chloride → HCID 178479845, compound

HRID 731051Notes

Reaction equation

HRID 731051 reaction equation
[CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][C:11]([C:15]3[CH:24]=[CH:23][C:18]([O:19][CH2:20][C:21]#[N:22])=[CH:17][CH:16]=3)=[CH:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2.[N-:25]=[N+:26]=[N-:27].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][N:2]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[C:11]([C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]3[NH:27][N:26]=[N:25][N:22]=3)=[CH:23][CH:24]=1)[CH:10]=2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68814430HCID 68814430, compound

Product 1

HCID 178479845HCID 178479845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 6 of example 3. Thus, [4-(9-methyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetonitrile (0.149 g, 0.471 mmol) was reacted with NaN3 (0.153 g, 2.355 mmol) and NH4Cl (0.126 g, 2.355 mmol) in DMF (5 ml) to give the product (0.060 g, 0.167 mmol, 35%) as a white solid, dec. 205-211° C. 1H NMR (DMSO-d6) δ 1.76-1.81 (m, 2H), 1.86-1.90 (m, 2H), 2.66 (t, J=6.0 Hz, 2H), 2.71 (t, J=5.8 Hz, 2H), 3.61 (s, 3H), 5.51 (s, 2H), 7.11 (d, J=8.7 Hz, 2H), 7.31 (dd, J=1.5, 8.4 Hz, 1H), 7.38 (d, J=8.4 Hz, 1H), 7.56 (s, 1H), 7.61 (d, J=8.7 Hz, 2H), 16.78 (broad s, 1H); IR (solid) 2930, 2850, 1520, 1480, and 1240 cm−1; [ESI(+)], m/z 360 (M+H)+; Anal. Calcd. for C21H21N5O: C, 70.18; H, 5.89; N, 19.48; Found: C, 69.94; H, 5.70; N, 19.67.

Sources & evidence

ORD record
ord-e5cc806500de4c41b36fde93f5e7ed5c
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

Loading…