2-Amino-6-benzothiazolol → [1-(2,6-Dichloropyridin-4-yl)ethoxy]-1,3-benzothiazol-2-amine

HRID 1929345Notes

Reaction equation

HRID 1929345 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[N:15]=[C:16]([NH2:18])[S:17][C:13]=3[CH:12]=2)[CH3:9])[CH:5]=[C:4]([Cl:21])[N:3]=1.NC1SC2C=C(O)C=CC=2N=1.BrCC1C=C(Cl)N=C(Cl)C=1>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([O:10][C:11]2[C:12]3[N:15]=[C:16]([NH2:18])[S:17][C:13]=3[CH:14]=[CH:19][CH:20]=2)[CH3:9])[CH:5]=[C:4]([Cl:21])[N:3]=1

Participants

4

Reactant 3

HCID 334622-Amino-6-benzothiazololHCID 27818294-(Bromomethyl)-2,6-dichloropyridineHCID 866469406-[1-(2,6-Dichloropyridin-4-yl)ethoxy]-1,3-benzothiazol-2-amine

Product 1

HCID 86646939[1-(2,6-Dichloropyridin-4-yl)ethoxy]-1,3-benzothiazol-2-amine

Procedure

6-[1-(2,6-Dichloropyridin-4-yl)ethoxy]-1,3-benzothiazol-2-amine can be prepared as in Example 8 but from 0.50 g of 2-amino-1,3-benzothiazol-6-ol and 0.723 g of 4-(bromomethyl)-2,6-dichloropyridine. After purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (95/5 by volume)], we obtain 306 mg of -[1-(2,6-dichloropyridin-4-yl)ethoxy]-1,3-benzothiazol-2-amine in the form of a beige solid, which has the following characteristics:

Workup

  1. customAfter purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (95/5 by volume)], we

Sources & evidence

ORD record
ord-86d21398677b452d8a10ec449bdccfca
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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