Pyridine → HCID 21997644, compound

HRID 1977118Notes

Reaction equation

HRID 1977118 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[S:19][CH2:20][C:21]#[N:22]>C1COCC1>[C:21]([CH2:20][S:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[NH:11][C:1](=[O:3])[CH3:2])#[N:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 21997643HCID 21997643, compound

Product 1

HCID 21997644HCID 21997644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (1.9 ml) in THF (10 ml) and subsequently pyridine (2.15 ml) in THF (10 ml) was added to a stirred solution of (2-amino-5-fluoro-phenylsulfanyl)acetonitrile (4.39 g) in THF (40 ml) at 0° C. The mixture was stirred at 0° C. for 1 h. Then the solvent was removed in vacuo and the residue was triturated with water (100 ml). The precipitate was filtered off and dried. Crude yield 4.45 g (82%); mp 97-100° C. The title compound could be further purified by recrystallization from 96% ethanol; mp 100.5-101.5° C.; 1H-NMR (DMSO-d6), δ (ppm): 9.68 (s, 1H, NH), 7.50-7.30 (m, 2H, Ar—H), 7.23-7.07 (m, 1H, Ar—H), 4.26 (s, 2H, CH2), 2.05 (s, 3H, CH3); IR (KBr) ν (cm−1): 3239 (NH), 2244 (C≡N), 1641 and 1579 (amide).

Workup

  1. customThen the solvent was removed in vacuo
  2. customthe residue was triturated with water (100 ml)
  3. filtrationThe precipitate was filtered off
  4. customdried
  5. customThe title compound could be further purified by recrystallization from 96% ethanol

Sources & evidence

ORD record
ord-965ef1402751402383cb799e2fe62297
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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