3,4-Dichloroaniline → HCID 71277766, compound

HRID 62119Notes

Reaction equation

HRID 62119 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][C:26]=1[Cl:27])N.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[Cl:19][C:20]1[CH:21]=[C:22]([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:25][C:26]=1[Cl:27]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 71277766HCID 71277766, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 3,4-dichloroaniline. Flash chromatography eluent (DCM-EtOAc, 7:3). Yield: 42%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 2851, 2225, 1644, 1612, 1579, 1456, 1378, 1355, 1308, 1270, 1241, 1168, 1122, 1026, 971, 879, 834, 816; 1H NMR (300 MHz, DMSO-d6) δ 8.55 (d, 1H, J=8.7 Hz), 8.30 (s, 1H), 7.78 (d, 1H, J=8.7 Hz), 7.63-7.53 (m, 2H), 7.30 (m, 2H); HRMS calcd for C16H8N5SCl2 (M+H+): 371.9877, found 371.9882.

Sources & evidence

ORD record
ord-f8cf3b3aac234197913c0b24aab1e8fd
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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