Triethylamine → HCID 19384277, compound

HRID 2399730Notes

Reaction equation

HRID 2399730 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([S:11][CH2:12][CH2:13][CH:14]=[C:15]([F:17])[F:16])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(=[O:21])[CH2:19][CH3:20].C(N(CC)CC)C>ClCCl>[O:21]=[C:18]([NH:1][C:2]1[C:7]2[N:8]=[C:9]([S:11][CH2:12][CH2:13][CH:14]=[C:15]([F:17])[F:16])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 19384307HCID 19384307, compound

Product 1

HCID 19384277HCID 19384277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-amino-2-(4,4-difluorobut-3-enylthio)benzoxazole (Compound No 80, Example 4B(iv), 255 mg) in dichloromethane (2 cm3) and propionyl chloride (102 mg) at the ambient temperature was added dropwise triethylamine (120 mg) and the reaction stirred for 31/2 hours, after which gc analysis indicated complete consumption of starting material. The reaction mixture was poured into ethyl acetate and water and the phases separated. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers washed with water and brine and then dried (MgSO4). Filtration and evaporation under reduced pressure gave a brown oil. Purification by silica gel chromatography using 30% t-butyl methyl ether in hexane as the eluent gave 4-(1-oxopropylamino)-2-(4,4-difluorobut-3-enylthio)benzoxazole as a pale yellow oil (124 mg). 1H NMR (DMSO): δ8.28(1H,d); 7.97(1H, b); 7.24(1H,t); 7.16(1H,d); 4.32(1H, ddt); 3.33(2H,t); 2.55(4H,m); 1.29(3H,t).

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was poured into ethyl acetate and water
  3. customthe phases separated
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washthe combined organic layers washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation under reduced pressure
  8. customgave a brown oil
  9. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-468757580a8a4c558c6317f493739147
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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