4,5-Dihydro-2-thiazolamine → HCID 178522560, compound
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:20]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([C:34]=1[OH:35])=[CH:32][CH:31]=[CH:30][CH:29]=2)(OCC)=[O:21]>C1(C)C=CC=CC=1>[S:16]1[CH2:17][CH2:18][N:19]=[C:15]1[NH:14][C:20]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([C:34]=1[OH:35])=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 8 °C
Procedure
167 ml of a solution of 25% by weight of triisobutyl aluminum in toluene were added with stirring over 20 minutes at 8° to 10° C. to a mixture of 37.4 g of 2-amino-thiazoline and 800 ml of methylene chlorideand the mixture was stirred at 8° C. for 30 minutes. 15.89 g of 3-carbethoxy-4-hydroxy-quinoline were added to the mixture which was then stirred for 30 minutes and then refluxed for 16 hours. The mixture was evaporated to dryness under reduced pressure and the residue was taken up in 1 liter of N aqueous hydrochloric acid. The solution was filtered and the filtrate was iced for 16 hours and was filtered. The product was washed with water and the filtrate was made alkaline with sodium carbonate. The mixture was filtered and the product was washed with water and dried to obtain 11.7 g of N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamide.
Workup
- stirringwas then stirred for 30 minutes
- temperaturerefluxed for 16 hours
- customThe mixture was evaporated to dryness under reduced pressure
- filtrationThe solution was filtered
- waitthe filtrate was iced for 16 hours
- filtrationwas filtered
- washThe product was washed with water
- filtrationThe mixture was filtered
- washthe product was washed with water
- customdried
Sources & evidence
- ORD record
- ord-4c8a3f2d8a3d4e5a8552b8818a29e9f4
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04450166
Reaction notes
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