4-Chloroaniline → HCID 71277765, compound

HRID 62118Notes

Reaction equation

HRID 62118 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].[Cl:19][C:20]1[CH:26]=[CH:25][C:23](N)=[CH:22][CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([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:22][CH:21]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 71277765HCID 71277765, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-chloroaniline. Flash chromatography eluent (DCM-EtOAc, 5:5). Yield: 89%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 2850, 2229, 1643, 1609, 1583, 1550, 1491, 1480, 1457, 1377, 1355, 1307, 1270, 1214, 1164, 1130, 1092, 1010, 980, 831; 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, 1H, J=8.7 Hz), 8.18 (s, 1H), 7.76 (d, 1H, J=8.7 Hz), 7.38 (m, 2H), 7.04 (m, 2H); HRMS calcd for C16H9N5SCl (M+H+): 338.0267, found 338.0274.

Sources & evidence

ORD record
ord-dd758b387deb48639fbf0bafcaaefe88
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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