[4-(5-Chloro-2-cyanophenoxy)-4-(2-thiazolyl)butyl]carbamic acid 1,1-dimethylethyl ester → 2-[4-Amino-1-(2-thiazolyl)butoxy]-4-chlorobenzonitrile hydrochloride

HRID 352143Notes

Reaction equation

HRID 352143 reaction equation
CC(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH:11]([O:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[C:25]#[N:26])[C:12]1[S:13][CH:14]=[CH:15][N:16]=1)(C)C>Cl.O1CCOCC1>[ClH:24].[NH2:7][CH2:8][CH2:9][CH2:10][CH:11]([C:12]1[S:13][CH:14]=[CH:15][N:16]=1)[O:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[C:25]#[N:26]

Participants

4

Reactant 1

HCID 70153671[4-(5-Chloro-2-cyanophenoxy)-4-(2-thiazolyl)butyl]carbamic acid 1,1-dimethylethyl ester

Product 1

HCID 227151012-[4-Amino-1-(2-thiazolyl)butoxy]-4-chlorobenzonitrile hydrochlorideYield 65.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from step (d) (0.20 g) was dissolved in 4M hydrochloric acid in dioxan (5 ml) and stirred for 3hat room temperature. The solvent was evaporated and the residue triturated with dry diethyl ether to give the title compound as a pale yellow solid (0.055 g). M.p 170-172° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with dry diethyl ether

Sources & evidence

ORD record
ord-a1d87e90e87f417188e4fd7110ca6653
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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