Acetyl chloride → HCID 11268197, compound

HRID 636849Notes

Reaction equation

HRID 636849 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[C:11]([CH:15]3[CH2:20][CH2:19][O:18][CH:17](C#N)[CH2:16]3)[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.C[CH2:24][N:25](CC)CC.[C:30](Cl)(=[O:32])[CH3:31]>CCOC(C)=O>[C:24]([C:15]1([C:11]2[CH:10]=[C:9]([S:8][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:30](=[O:32])[CH3:31])=[CH:7][CH:6]=3)[CH:14]=[CH:13][CH:12]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)#[N:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21255963HCID 21255963, compound

Product 1

HCID 11268197HCID 11268197, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
55 °C

Procedure

4-[3-(4-amino-phenyl sulfanyl)-phenyl]-tetrahydro-pyran-carbonitrile (93.57 g) and Et3N (53.1 mL) were dissolved in EtOAc (1.23 L) and heated to 50-60° C. To this solution was added acetylchloride (27.7 ml) in EtOAc (73 mL) over 30 minutes. The suspension obtained was filtered and the filter cake was washed with EtOAc (3×150 mL). The combined EtOAc solutions were washed with water (0.5 L), half saturated aqueous Na2CO3 (2×0.5 L), water (0.5 L) and saturated aqueous NaCl (0.25 L). The organics were dried with Na2SO4 and evaporated at 40° C. The crude product was recrystallized from refluxing EtOH (0.52 L) to give after cooling, filtration and drying at 40° C./20 mbar, N-{4-[3-(4-Cyano-tetrahydro-pyran-4yl)-phenyl sulfanyl]-phenyl}acetamide (55.27 g, 52% yield).

Workup

  1. customThe suspension obtained
  2. filtrationwas filtered
  3. washthe filter cake was washed with EtOAc (3×150 mL)
  4. washThe combined EtOAc solutions were washed with water (0.5 L), half saturated aqueous Na2CO3 (2×0.5 L), water (0.5 L) and saturated aqueous NaCl (0.25 L)
  5. dry with materialThe organics were dried with Na2SO4
  6. customevaporated at 40° C
  7. customThe crude product was recrystallized
  8. temperaturefrom refluxing EtOH (0.52 L)
  9. customto give
  10. temperatureafter cooling
  11. filtrationfiltration

Sources & evidence

ORD record
ord-416e655c91a14b83823f96247b2b69f9
Source dataset
uspto-grants-2001_02
Patent number
US06194585B1

Reaction notes

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