Water → 2-[(2-Chloro-1,3-benzothiazol-6-yl)oxy]-N,N-diethylethan-1-amine

HRID 581055Notes

Reaction equation

HRID 581055 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17]Cl)[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH2:14][CH2:13][N:15]([CH2:19][CH3:20])[CH2:16][CH3:17])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 147498432-Chlorobenzo[d]thiazol-6-ol

Product 1

HCID 158176322-[(2-Chloro-1,3-benzothiazol-6-yl)oxy]-N,N-diethylethan-1-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.15 g (16.7 mmol) of 2-chloro-6-hydroxy-benzothiazole are dissolved in 50 ml of dimethylformamide and after the addition of 5.68 g (33 mmol) of 2-diethylamino-ethyl chloride-hydrochloride and 8.3 g (60 mmol) of potassium carbonate the mixture was stirred for 20 hours at ambient temperature. It was then added to water and extracted with ethyl acetate. The extracts are dried and evaporated down. The evaporation residue is purified by column chromatography on neutral aluminium oxide (eluant: petroleum ether/ethyl acetate=6:1). Yield: 3.9 g (81.7% of theory), oil, 1H-NMR spectrum (200 MHz, CDCl3, signals at ppm): 1.08 (t, 6H); 2.65 (q, 4H); 2.9 (t, 2H); 4.09 (t, 2H); 7.08 (dd, 1H); 7.24 (d, 1H); 7.8 (d, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extracts are dried
  3. customevaporated down
  4. customThe evaporation residue is purified by column chromatography on neutral aluminium oxide (eluant: petroleum ether/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-88f7249e8697472dab3bec84acb6081b
Source dataset
uspto-grants-1999_07
Patent number
US05919807

Reaction notes

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