Sodium hydride → 3-Acetyl-2-[2-(3-dimethylaminopropoxy)phenyl]benzothiazoline

HRID 1583662Notes

Reaction equation

HRID 1583662 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].[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]Cl>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][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 133359603-Acetyl-2-(2-hydroxyphenyl)benzothiazoline

Product 1

HCID 133357593-Acetyl-2-[2-(3-dimethylaminopropoxy)phenyl]benzothiazolineYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To the suspension of 0.26 g of the sodium hydride in anhydrous DMF, the solution of 1.36 g of 3-acetyl-2-(2-hydroxyphenyl)benzothiazoline in 5 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 0.61 g of 3-dimethylaminopropyl chloride in 10 ml of anhydrous DMF is added. The reaction mixture is stirred for 2 hours at 80° C., and washed with n-hexane after cooling and poured into ice-water. The separated oil is extracted with ethyl acetate. The organic layer is washed with N--NaOH solution, water and saturated sodium chloride solution in the order named and dried over anhydrous magnesium sulfate. Ethy acetate is removed off in vacuo to give 1.0 g (56%) of the titled compound.

Workup

  1. additionAfter the addition
  2. stirringThe reaction mixture is stirred for 2 hours at 80° C.
  3. washwashed with n-hexane
  4. temperatureafter cooling
  5. additionpoured into ice-water
  6. extractionThe separated oil is extracted with ethyl acetate
  7. washThe organic layer is washed with N
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customEthy acetate is removed off in vacuo

Sources & evidence

ORD record
ord-843d9fe9fbcc4a24a3031fab2a6bbfba
Source dataset
uspto-grants-1985_11
Patent number
US04552969

Reaction notes

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