Ammonium Chloride → HCID 178420300, compound

HRID 731045Notes

Reaction equation

HRID 731045 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([C:21]3[CH:30]=[CH:29][C:24]([O:25][CH2:26][C:27]#[N:28])=[CH:23][CH:22]=3)=[CH:16][C:15]=2[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:31]=[N+:32]=[N-:33].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([N:8]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[C:15]2[C:20]1=[CH:19][CH:18]=[C:17]([C:21]1[CH:22]=[CH:23][C:24]([O:25][CH2:26][C:27]3[NH:33][N:32]=[N:31][N:28]=3)=[CH:29][CH:30]=1)[CH:16]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68817359[4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetonitrile

Product 1

HCID 178420300HCID 178420300, 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-benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetonitrile (0.357 g, 0.910 mmol) was reacted with NaN3 (0.296 g, 4.548 mmol) and NH4Cl (0.243 g, 4.548 mmol) in DMF (10 ml) to give the product (0.329 g, 0.755 mmol, 83%) as a white solid, dec. 228-230° C. 1H NMR (DMSO-d6) δ 1.79-1.85 (m, 4H), 2.64-2.71 (m, 4H), 5.33 (s, 2H), 5.50 (s, 2H), 7.03 (d, J=7.6 Hz, 2H), 7.11 (d, J=8.7 Hz, 2H), 7.21 (t, J=7.2 Hz, 1H), 7.27-7.30 (m, 3H), 7.39 (d, J=8.6 Hz, 1H), 7.59-7.61 (m, 3H), 16.80 (broad s, 1H); IR (solid) 3030, 2920, 2590, 1520, 1470 and 1240 cm−1; [ESI(+)], m/z 436 (M+H)+; Anal. Calcd. for C27H25N5O: C, 74.46; H, 5.79; N, 16.08; Found: C, 74.34; H, 5.46; N, 16.26.

Sources & evidence

ORD record
ord-f35e97de95b94bbd911f6bd3b4712cd4
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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