Pyridine → HCID 21997651, compound

HRID 1977115Notes

Reaction equation

HRID 1977115 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[NH2:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=1[S:20][CH2:21][C:22]#[N:23]>C1COCC1>[C:22]([CH2:21][S:20][C:13]1[CH:14]=[C:15]([F:19])[CH:16]=[C:17]([F:18])[C:12]=1[NH:11][C:1](=[O:3])[CH3:2])#[N:23]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 6367Acetyl chloride2×HCID 21997650HCID 21997650, compound

Product 1

HCID 21997651HCID 21997651, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (575 μl, 8 mmol) in THF (2 ml) and subsequently pyridine (645 μl, 8 mmol) in THF (2 ml) were added to a stirred solution of (2-amino-3,5-difluorophenylsulfanyl)acetonitrile (1.53 g) in THF (20 ml) at 0° C. The mixture was stirred at 0° C. for 15 min, then at ambient temperature for 1 h. Additional amounts of acetyl chloride (57 μl) and pyridine (65 μl) were added, and stirring was continued for 1 h. Then the solvent was removed in vacuo and the residue was triturated with water (25 ml). The precipitate was filtered off and dried. Recrystallization from 96% ethanol gave the title compound. Yield 1.16 g (63%), mp 148.5-149° C. An additional crop of the title compound (0.25 g, 13%) was obtained from the mother liqueor; 1H-NMR (DMSO-d6), δ (ppm): 9.65 (s, 1H, NH), 7.40-7.20 (m, 2H, Ar—H), 4.34 (s, 2H, CH2), 2.09 (s, 3H, CH3).

Workup

  1. waitat ambient temperature for 1 h
  2. stirringstirring
  3. waitwas continued for 1 h
  4. customThen the solvent was removed in vacuo
  5. customthe residue was triturated with water (25 ml)
  6. filtrationThe precipitate was filtered off
  7. customdried
  8. customRecrystallization from 96% ethanol

Sources & evidence

ORD record
ord-4d064dc076c94318aa7330520ac4fde4
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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