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

HRID 1633242

Reaction equation

HRID 1633242 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-c5771f61252e4acf97aad10b32e1b75f
Source dataset
uspto-grants-1984_10
Patent number
US04479949

Linked notes

Loading…