4-Amino-2,6-dichlorophenol → 3,5-Dichloro-4-(4-methoxy-benzothiazol-2-yloxy)-phenylamine

HRID 1819804Notes

Reaction equation

HRID 1819804 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1.[NH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([OH:21])=[C:16]([Cl:22])[CH:15]=1>>[Cl:20][C:18]1[CH:19]=[C:14]([NH2:13])[CH:15]=[C:16]([Cl:22])[C:17]=1[O:21][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1

Participants

3

Reactant 2

HCID 800374-Amino-2,6-dichlorophenolHCID 20498622-Chloro-4-methoxy-1,3-benzothiazole

Product 1

HCID 185115003,5-Dichloro-4-(4-methoxy-benzothiazol-2-yloxy)-phenylamine

Procedure

3,5-Dichloro-4-(4-methoxy-benzothiazol-2-yloxy)-phenylamine was synthesized (21%) from 2-chloro-4-methoxybenzotiazole (257) and 4-amino-2,6-dichlorophenol (Aldrich) in a similar manner as described in Example 417. 1H NMR (400 MHz, DMSO-d6) δ 7.48 (d, J=8.0 Hz, 1H), 7.28 (t, J=8.1 Hz, 1H), 7.01 (d, J=8.1 Hz, 1H), 6.73 (s, 2H), 5.86 (s, 2H), 3.85 (s, 3H). MS (EI): m/z 341 (M+H).

Sources & evidence

ORD record
ord-eff893d5539745679417245eb539ad00
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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