Sodium hydride → HCID 178457776, compound

HRID 598206Notes

Reaction equation

HRID 598206 reaction equation
[C:1]([CH2:3][C:4]([N:6]([CH:17]([CH3:19])[CH3:18])[C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([SH:14])[S:13][C:9]=2[CH:8]=1)=[O:5])#[N:2].[H-].[Na+].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C1COCC1>[C:1]([C:3](=[C:28]([OH:29])[C:27]1[CH:31]=[CH:32][C:24]([C:23]([F:22])([F:33])[F:34])=[CH:25][CH:26]=1)[C:4]([N:6]([CH:17]([CH3:19])[CH3:18])[C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([SH:14])[S:13][C:9]=2[CH:8]=1)=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 178457774HCID 178457774, compound

Product 1

HCID 178457776HCID 178457776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cooled a 0.1 M solution of α-cyano-N-isopropyl-N-(2-mercaptobenzothiazol-6-yl)acetamide (50 mg, 0.172 mmol) in anhydrous THF to 0° C. Added 60% sodium hydride in mineral oil (69 mg, 1.720 mmol) and stirred 15 minutes. 4-(trifluoromethyl)benzoyl chloride (36 μl, 0.189 mmol) was added dropwise and the mixture stirred an additional 30 minutes. The reaction was quenched by addition of 0.1 M aqueous HCl. The mixture was extracted with ethyl acetate three times, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (5% methanol, 95% dichloromethane) to yield 27 mg (34%). 1H NMR (CDCl3) δ1.17 (d, 6H), 5.01 (m, 1H), 7.12 (d, 1H), 7.21 (dd, 1H), 7.31 (s, 1H), 7.64 (app q, 4H); ESIMS: m/z 462 (M-H).

Workup

  1. stirringthe mixture stirred an additional 30 minutes
  2. customThe reaction was quenched by addition of 0.1 M aqueous HCl
  3. extractionThe mixture was extracted with ethyl acetate three times
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (5% methanol, 95% dichloromethane)
  7. customto yield 27 mg (34%)

Sources & evidence

ORD record
ord-78599168d46d46419627ff6634baf840
Source dataset
uspto-grants-2011_03
Patent number
US07897615B2

Reaction notes

Loading…