2-Aminothiazole → HCID 178522554, compound

HRID 1650711Notes

Reaction equation

HRID 1650711 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Al](CC(C)C)CC(C)C)C(C)C.[C:20]1([C:26]2[C:27]([OH:47])=[C:28]([C:42](OCC)=[O:43])[C:29]([C:38]([F:41])([F:40])[F:39])=[N:30][C:31]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[C:20]1([C:26]2[C:27]([OH:47])=[C:28]([C:42]([NH:1][C:2]3[S:3][CH:4]=[CH:5][N:6]=3)=[O:43])[C:29]([C:38]([F:40])([F:41])[F:39])=[N:30][C:31]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 16682931TriisobutylaluminumHCID 178469139HCID 178469139, compound

Product 1

HCID 178522554HCID 178522554, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

3.22 g of 2-aminothiazole were cooled to +2° C. in 80 ml of methylene chloride, and while maintaining the temperature between +2° and +5° C. 17.9 ml of triisobutyl aluminium in toluene (0.9M) were added and stirred for 20 minutes. 2.5 g of the product of Step D were then introduced all at once into the mixture and the temperature was brought up progressively to reflux and kept there for 24 hours then lowered to the ambient. The mixture was concentrated to dryness under reduced pressure and 50 ml of water and 50 ml of 2N hydrochloric acid were added to the residue. The mixture was triturated and the precipitate was separated and washed abundantly with water. While still humid, the latter was dissolved in tetrahydrofuran and the solution was dried and concentrated under reduced pressure. The 2.6 g of residue were triturated in ether, separated and dried to obtain 2.05 g of product melting at 256° C. After crystallizing from acetonitrile, 1.48 g of the expected product melted at 256° C.

Workup

  1. temperaturewhile maintaining the temperature between +2° and +5° C
  2. temperatureto reflux
  3. waitkept there for 24 hours
  4. concentrationThe mixture was concentrated to dryness under reduced pressure and 50 ml of water and 50 ml of 2N hydrochloric acid
  5. additionwere added to the residue
  6. customThe mixture was triturated
  7. customthe precipitate was separated
  8. washwashed abundantly with water
  9. dissolutionWhile still humid, the latter was dissolved in tetrahydrofuran
  10. customthe solution was dried
  11. concentrationconcentrated under reduced pressure
  12. customThe 2.6 g of residue were triturated in ether
  13. customseparated
  14. customdried

Sources & evidence

ORD record
ord-9cf8c9b581324b628d0a740e338eed0e
Source dataset
uspto-grants-1990_05
Patent number
US04925859

Reaction notes

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