Triethylamine → HCID 137175501, compound

HRID 1248814Notes

Reaction equation

HRID 1248814 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([N:8]([CH2:11][CH3:12])CC)C.[F:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:15]=1[C:16](Cl)=[O:17]>C1C=CC=CC=1.CN(C)C1C=CN=CC=1.C(Cl)Cl>[OH:17][C:16]([C:15]1[C:14]([F:13])=[CH:22][CH:21]=[CH:20][C:19]=1[F:23])=[C:12]([C:2]1[S:1][CH:5]=[C:4]([C:15]([CH3:19])([CH3:16])[CH3:14])[N:3]=1)[C:11]#[N:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 9256ThiazoleHCID 874382,6-Difluorobenzoyl chloride

Product 1

HCID 137175501HCID 137175501, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

Acylation with One Equivalent of Acid Chloride. A mixture of 2.0 g of the thiazole of Embodiment 16, and 2.1 ml of triethylamine in 25 ml of benzene was treated with 2.0 g of 2,6-difluorobenzoyl chloride. After stirring overnight at room temperature with exclusion of ambient atmosphere, a catalytic amount of 4-dimethylaminopyridine, 0.2 g, was added, and stirring was continued for another 24 hours. At this point the mixture was diluted to 100 ml with methylene chloride and washed with water. The organic layer was dried (MgSO4) and concentrated. The resultant brown oil was taken up in 100 ml methanol, treated with 2 drops of concentrated H2SO4, and refluxed for 5 hours. When this solution was cooled and poured into 200 ml of water, the product crystallized. Filtration afforded 2.9 g of the desired product; m.p. 207°-208.5° C.

Workup

  1. stirringstirring
  2. waitwas continued for another 24 hours
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. additiontreated with 2 drops of concentrated H2SO4
  7. temperaturerefluxed for 5 hours
  8. temperatureWhen this solution was cooled
  9. additionpoured into 200 ml of water
  10. customthe product crystallized
  11. filtrationFiltration

Sources & evidence

ORD record
ord-a3948cc8bd9341bfb0fd03613d9e06e6
Source dataset
uspto-grants-1986_12
Patent number
US04626543

Reaction notes

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