1,2-Dichloroethane → HCID 20190397, compound

HRID 1788758Notes

Reaction equation

HRID 1788758 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]3[CH2:12][S:13][CH2:14][C:10]3=[C:9]([C:15]([OH:17])=O)[CH:8]=2)[CH:2]=1.CN(C)C=O.[Cl:23]CCCl>S(Cl)(Cl)=O.C1CCCCC1>[ClH:23].[Cl:23][C:15]([C:9]1[CH:8]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:11]2[C:10]=1[CH2:14][S:13][CH2:12]2)=[O:17]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 13375484HCID 13375484, compound

Product 1

HCID 20190397HCID 20190397, compound

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid (8.8 g) in a mixture of thionyl chloride (6.25 cc), dimethylformamide (0.05 cc) and 1,2dichloroethane (100 cc) is heated under reflux with stirring for 2 hours and 30 minutes. The reaction mixture is cooled to a temperature of about 20° C. and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. The residue obtained is suspended in cyclohexane (150 cc) and the solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. The same procedure is repeated twice. 7- Chloroformyl-5-(3-pyridyl)-pyrrolo[1,2-c]thiazole hydrochloride (10 g) is thus obtained in the form of cream crystals melting at 220° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C
  4. customThe residue obtained
  5. customthe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C

Sources & evidence

ORD record
ord-94d50d7044474d4f8c6033ec795dc15c
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

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