Dichloromethane → HCID 178435575, compound

HRID 544393Notes

Reaction equation

HRID 544393 reaction equation
C([Al](CC(C)C)CC(C)C)C(C)C.[NH2:14][C:15]1[S:16][CH2:17][CH2:18][N:19]=1.C(Cl)[Cl:21].C([C:25]1[C:34]([C:35](N)=[O:36])=[C:33]([OH:38])[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([CH2:39][CH3:40])[CH:31]=2)[N:26]=1)C>C1(C)C=CC=CC=1>[ClH:21].[S:16]1[CH2:17][CH2:18][N:19]=[C:15]1[NH:14][C:35]([C:34]1[CH:25]=[N:26][C:27]2[C:32]([C:33]=1[OH:38])=[CH:31][C:30]([CH2:39][CH3:40])=[CH:29][CH:28]=2)=[O:36]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 156894,5-Dihydro-2-thiazolamineHCID 16682931TriisobutylaluminumHCID 178435574HCID 178435574, compound

Product 1

HCID 178435575HCID 178435575, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

45.36 ml of 1.1 M of triisobutyl aluminum in toluene were added with stirring over 10 minutes at 7° to 10° C. to a mixture of 10.2 g of 2-amino-thiazoline and 500 ml of methylene chloride and the mixture was stirred at 7° to 10° C. for one hour. 4.88 of ethyl 6-ethyl-4-hydroxy-3-quinolin-carboxamide were added to the mixture which was then refluxed for 16 hours. The mixture was evaporated to dryness under reduced pressure and the residue was taken up to 100 ml of aqueous N hydrochloric acid solution. The solution was heated at 70° C. for 2 hours and was treated with activated carbon and filtered. The filtrate was allowed to crystallize and was then vacuum filtered. The recovered product was washed with aqueous N hydrochloric acid solution and was dried under reduced pressure and crystallized from acetic acid to obtain 2.2 g of N-(4,5-dihydro-thiazol-2-yl)-6-ethyl-4-hydroxy-3 -quinoline-carboxamide hydrochloride melting at >260° C.

Workup

  1. temperaturewas then refluxed for 16 hours
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. additionwas treated with activated carbon
  4. filtrationfiltered
  5. customto crystallize
  6. filtrationvacuum filtered
  7. washThe recovered product was washed with aqueous N hydrochloric acid solution
  8. customwas dried under reduced pressure
  9. customcrystallized from acetic acid

Sources & evidence

ORD record
ord-23281665b39544c8aef68b8d6b10991a
Source dataset
uspto-grants-1984_05
Patent number
US04450166

Reaction notes

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