3-Chloroaniline → HCID 71277756, compound

HRID 62135Notes

Reaction equation

HRID 62135 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:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)N.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[Cl:19][C:20]1[CH:26]=[C:25]([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:24]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 71277756HCID 71277756, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 3-chloroaniline. Flash chromatography eluent (DCM-EtOAc, 7:3). Yield: 74%; pale yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 2849, 2226, 1643, 1611, 1577, 1461, 1377, 1354, 1306, 1218, 1161, 1128, 1070, 974, 875, 833; 1H NMR (300 MHz, DMSO-d6) δ 8.49 (d, 1H, J=9.0 Hz), 8.21 (s, 1H), 7.74 (d, 1H, J=9.0 Hz), 7.40-7.35 (m, 2H), 7.19-7.11 (m, 2H); HRMS calcd for C16H9N5SCl (M+H+): 338.0267, found 338.0259.

Sources & evidence

ORD record
ord-e1d49890ca924388a327f1086a2198df
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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