Chloroacetyl chloride → 1-(Chloroacetyl)pyrrolidine

HRID 1954207Notes

Reaction equation

HRID 1954207 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:10][C:11]1[N:12]=[CH:13][S:14][C:15]=1[CH3:16].N1CCCC1.ClCC(Cl)=O.[OH-].[Na+]>C(Cl)Cl>[Cl-:1].[N:5]1([C:3](=[O:4])[CH2:2][N+:12]2[C:11]([CH3:10])=[C:15]([CH3:16])[S:14][CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1.[Cl:1][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

8

Reactant 5

HCID 6577Chloroacetyl chloride2×HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 625104,5-DimethylthiazoleHCID 884401-(Chloroacetyl)pyrrolidine

Product 2

HCID 884401-(Chloroacetyl)pyrrolidineHCID 99431363-(2-(1-Pyrrolidinyl)-2-oxoethyl)-4,5-dimethyl-thiazolium chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(2-(1-pyrrolidinyl)-2-oxoethyl)-4,5-dimethyl-thiazolium chloride was prepared from the reaction of N-(chloroacetyl)pyrrolidine with 4,5-dimethylthiazole. N-(chloroacetyl)pyrrolidine was prepared as follows. Pyrrolidine (63.9 g. 0.9 mol) was taken in methylene chloride (640 mL) and cooled to 0° C. in a salt-ice bath. To the stirred mixture was added chloroacetyl chloride (101.8 g in 450 mL of CH2Cl2, 0.9 mol) dropwise keeping the inside temperature below 15° C. After adding the chloroacetyl chloride, the mixture was stirred for an hour at 5° C. Sodium hydroxide solution (7 M, 190 mL) was added with vigorous stirring such that the inside temperature did not exceed 20° C. The mixture was stirred for 15 minutes and the aqueous layer was separated. The organic layer was washed successively with saturated sodium bicarbonate solutions (2×200 mL), water (1×200 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was recrystallized from hexane to give 64.5 g (48.6%) of white plate crystals, m.p. 43° C.

Workup

  1. customthe inside temperature below 15° C
  2. stirringwith vigorous stirring such that the inside temperature
  3. customdid not exceed 20° C
  4. stirringThe mixture was stirred for 15 minutes
  5. customthe aqueous layer was separated
  6. washThe organic layer was washed successively with saturated sodium bicarbonate solutions (2×200 mL), water (1×200 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue was recrystallized from hexane
  10. customto give 64.5 g (48.6%) of white plate crystals, m.p. 43° C.

Sources & evidence

ORD record
ord-6f1c5f12a3bb498487027265ff81a702
Source dataset
uspto-grants-2000_09
Patent number
US06121300

Reaction notes

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