2,6-Dichlorobenzothiazole → 3,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine

HRID 2422467Notes

Reaction equation

HRID 2422467 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([OH:20])=[C:15]([Cl:21])[CH:14]=1>>[Cl:19][C:17]1[CH:18]=[C:13]([NH2:12])[CH:14]=[C:15]([Cl:21])[C:16]=1[O:20][C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

3

Reactant 2

HCID 771762,6-DichlorobenzothiazoleHCID 800374-Amino-2,6-dichlorophenol

Product 1

HCID 221487763,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine

Procedure

3,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine was synthesized (65%) from 2,6-dichlorobenzothiazole (259) and 4-amino-2,6-dichlorophenol (Aldrich) in a similar manner as described in Example 417. 1H NMR (400 MHz, DMSO-d6) δ 8.10 (d, J=2.2 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.47 (dd, J=8.7, 2.2 Hz, 1H), 6.73 (s, 2H), 5.88 (s, 2H). MS (EI): m/z 345 (M+H).

Sources & evidence

ORD record
ord-81ccb03f16ff46eca7fd198b1a02ea4b
Source dataset
uspto-grants-2011_06
Patent number
US07960408B2

Reaction notes

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