4-Aminobenzonitrile → HCID 71277788, compound

HRID 62130Notes

Reaction equation

HRID 62130 reaction equation
[C:1]([C:3]1[S:4][C:5]2[C:11]([C:12]#[N:13])=[C:10](/[N:14]=[CH:15]/[N:16](C)C)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].N[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[C:24]([C:23]1[CH:26]=[CH:27][C:20]([NH:13][C:12]2[C:11]3[C:10](=[CH:9][CH:8]=[C:6]4[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]4=3)[N:14]=[CH:15][N:16]=2)=[CH:21][CH:22]=1)#[N:25]

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 71277788HCID 71277788, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-aminobenzonitrile. Flash chromatography eluent (DCM-EtOAc, 5:5). Yield: 36%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3293, 2225, 2218, 1722, 1628, 1590, 1562, 1495, 1461, 1387, 1261, 1228, 1132, 966, 847, 814; 1H NMR (300 MHz, DMSO-d6) δ 8.54 (d, 1H, J=9.0 Hz), 8.28 (s, 1H), 7.77 (m, 3H), 7.40 (d, 2H, J=9.0 Hz); HRMS calcd for C17H9N6S (M+H+): 329.0609, found 329.0612.

Sources & evidence

ORD record
ord-048c18ebb2a046f79e81f679e2122cf3
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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