Phosphorus pentachloride → 1-(4-(chloromethyl)thiazol-2-yl)-N,N-dimethylmethanamine hydrochloride

HRID 358521Notes

Reaction equation

HRID 358521 reaction equation
[Cl:1][CH2:2][C:3]1(O)[CH2:7][S:6][C:5]([CH2:8][N:9]([CH3:11])[CH3:10])=[N:4]1.P(Cl)(Cl)(Cl)(Cl)Cl>ClCCCl>[ClH:1].[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:8][N:9]([CH3:11])[CH3:10])[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 103307024-Thiazolol, 4-(chloromethyl)-2-[(dimethylamino)methyl]-4,5-dihydro-

Product 1

HCID 131219581-(4-(chloromethyl)thiazol-2-yl)-N,N-dimethylmethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a 100 ml. flask were added 2.1 g. of 4-chloromethyl-4-hydroxy-2-dimethylaminomethyl-2-thiazoline and 25 ml. of 1,2-dichloroethane. To the mixture was added dropwise a solution of 2.1 g. of phosphorous pentachloride and 50 ml. of 1,2-dichloroethane, while the temperature of the mixture was held in the range 17°-25°. After the addition, the mixture was stirred for 16 hours. It was then filtered, and the filter cake was washed with 1,2-dichloroethane and dried under vacuum at 50° to obtain 2.4 g. of the desired product, which was identified by nmr analysis as being substantially identical to the product of Example 5.

Workup

  1. additionflask were added 2.1 g
  2. additionTo the mixture was added dropwise a solution of 2.1 g
  3. customwas held in the range 17°-25°
  4. additionAfter the addition
  5. filtrationIt was then filtered
  6. washthe filter cake was washed with 1,2-dichloroethane
  7. customdried under vacuum at 50°
  8. customto obtain 2.4 g

Sources & evidence

ORD record
ord-a24153432fe049aba045169b4c6a6c21
Source dataset
uspto-grants-1984_08
Patent number
US04468517

Reaction notes

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