Benzoyl chloride → HCID 44600098, compound

HRID 1876907Notes

Reaction equation

HRID 1876907 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH2:11][S:10][C:9]2=[NH:13])=[CH:5][N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH2:11][S:10][C:9]2=[N:13][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 10198562HCID 10198562, compound

Product 1

HCID 44600098HCID 44600098, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

3-(2-Chloro-5-thiazolylmethyl)-2-iminothiazolidine (233 mg, 1.0 mmol) and sodium carbonate (120 mg, 1.1 mmol) were dissolved in 10 ml of water, into which, benzoyl chloride (141 mg, 1.0 mmol) dissolved in 5 ml of chloroform was added under cooling with ice, and thereafter stirred at room temperature for 2 hours. The chloroform layer was washed successively with 1% hydrochloric acid and water, dehydrated and dried, chloroform was distilled off, and remaining oil was purified by a silica gel column chromatography to obtain the intended substance. The crude crystal of the intended substance was recrystallized from ethyl acetate. Yield: 101 mg (30%). Melting point: 120° C.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. washThe chloroform layer was washed successively with 1% hydrochloric acid and water
  4. customdried
  5. distillationchloroform was distilled off
  6. customwas purified by a silica gel column chromatography
  7. customto obtain the intended substance
  8. customThe crude crystal of the intended substance was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9adc8a399f2546c78828f8e17b02d502
Source dataset
uspto-grants-2012_11
Patent number
US08309733B2

Reaction notes

Loading…