Sodium Iodide → HCID 70169838, compound

HRID 843091Notes

Reaction equation

HRID 843091 reaction equation
Cl[CH2:2][O:3][C:4]([N:6]([C:22](=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:24]=1[CH3:31])[N:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1)=[O:5].[I-:33].[Na+]>CC(C)=O>[I:33][CH2:2][O:3][C:4]([N:6]([C:22](=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:24]=1[CH3:31])[N:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1)=[O:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 70169813HCID 70169813, compound

Product 1

HCID 70169838HCID 70169838, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
30 °C

Procedure

A solution of N′-tert-butyl-N′-(3,5-dimethylbenzoyl)-N-(3-methoxy-2-methylbenzoyl)hydrazine carboxylic acid chloromethyl ester (15.0 g, 32.5 mmol) in 40 mL of acetone was added sodium iodide (9.8 g, 65.1 mmol)and heated to 30° C. for 3 h. The acetone was removed and the resulting slurry was treated with ether. The resulting white precipitated solids were filtered off, and the ether was then concentrated to afford yellow solids. Recrystallization from ether/hexanes afforded tannish crystals (20 g, 96%). 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.64 (s, 9H), 1.97 (bs, 3H), 2.25 (s, 6H), 3.79 (s, 3H), 5.76 (s, 2H), 6,78-7.1 (m, 6H). Mp=70-72° C.

Workup

  1. customThe acetone was removed
  2. additionthe resulting slurry was treated with ether
  3. customThe resulting white precipitated solids
  4. filtrationwere filtered off
  5. concentrationthe ether was then concentrated
  6. customto afford yellow solids
  7. customRecrystallization from ether/hexanes afforded tannish crystals (20 g, 96%)

Sources & evidence

ORD record
ord-1bc16df8e8d6482a9bb2a1015566ba18
Source dataset
uspto-grants-2002_04
Patent number
US06376548B1

Reaction notes

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