Ethyl 4-chlorobutyrate → 3-Acetyl-2-[2-[3-(ethoxycarbonyl)-propoxy]phenyl]benzothiazoline

HRID 637754

Reaction equation

HRID 637754 reaction equation
[H-].[Na+].[C:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])(=[O:5])[CH3:4].Cl[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[C:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 18474Ethyl 4-chlorobutyrateHCID 24758Sodium hydrideHCID 133359603-Acetyl-2-(2-hydroxyphenyl)benzothiazoline

Product 1

HCID 135642173-Acetyl-2-[2-[3-(ethoxycarbonyl)-propoxy]phenyl]benzothiazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To the suspension of 1.59 g of sodium hydride in 30 ml of anhydrous DMF, the solution of 8.13 g of 3-acetyl-2-(2-hydroxyphenyl)benzothiazoline in 30 ml of anhydrous DMF is added dropwise under nitrogen atmosphere at room temperature. After the addition, the reaction mixture is stirred for 20 minutes at room temperature. To the reaction mixture, the solution of 4.95 g of ethyl 4-chlorobutyrate in 15 ml of anhydrous DMF is added and stirred for 5 hours at 70° C. After cooling to room temperature the reaction mixture is poured into ice-water and extracted with ethyl acetate.

Workup

  1. additionAfter the addition
  2. stirringstirred for 5 hours at 70° C
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-172096d1e1094eb0acee96098768111b
Source dataset
uspto-grants-1985_12
Patent number
US04558125

Linked notes

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