Sodium hydride → HCID 22065212, compound

HRID 1835393Notes

Reaction equation

HRID 1835393 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[C:18]([CH3:19])=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[S:16][CH:15]=2)[N:11]([CH3:27])[N:10]=1.[H-].[Na+].I[CH2:31][CH2:32][CH3:33]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[C:18]([CH3:19])=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:31][CH2:32][CH3:33])=[CH:22][CH:21]=3)[S:16][CH:15]=2)[N:11]([CH3:27])[N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 336431-Iodopropane2×HCID 22065189HCID 22065189, compound

Product 1

HCID 22065212HCID 22065212, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 3-(2-chloro-6-fluorophenyl)-5-[5-(4-hydroxyphenyl)-4-methylthien -3-yl]-1-methyl-1H-1,2,4-triazole (97 mg, 0.2 mmol) in dry THF (2 mL) was cooled to −3° C. and treated with sodium hydride (95% suspension in mineral oil, 9 mg, 0.4 mmol). After stirring for 5 minutes, iodopropane (62 mg, 0.4 mmol) was added and the reaction was allowed to stir at room temperature for 16 hours. An additional batch of sodium hydride (9 mg, 0.4 mmol) and iodopropane (62 mg, 0.4 mmol) was added and the reaction heated to 45° C. After dilution with water (5 mL), the product was extracted with ether (3×5 mL). The combined ethereal extracts were washed with water (2×5 mL) and brine (10 mL), dried over magnesium sulphate and concentrated. Column chromatography gave the product (101 mg, 93%) as a colorless glass: 1H NMR (CDCl3) δ 7.49 (s, 1H), 7.27-7.41 (m, 4H), 7.12 (t, 1H), 6.98 (d, 2H), 4.04 (s, 3H), 3.99 (t, 2H), 2.32 (s, 3H), 1.85 (m, 2H), 1.08 (t, 3H); EI/MS 441 m/e (M+1).

Workup

  1. stirringto stir at room temperature for 16 hours
  2. extractionAfter dilution with water (5 mL), the product was extracted with ether (3×5 mL)
  3. washThe combined ethereal extracts were washed with water (2×5 mL) and brine (10 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0d0a4c6ed2f547b5b3c5d6ed4b9c2cf8
Source dataset
uspto-grants-2004_08
Patent number
US06770665B2

Reaction notes

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