Triethylamine → HCID 21071758, compound

HRID 1372473Notes

Reaction equation

HRID 1372473 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[I:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([NH:19][NH2:20])=[O:18].C(N(CC)CC)C>C1COCC1>[I:13][C:14]1[CH:15]=[C:16]([C:17]2[O:18][C:6](=[O:7])[NH:20][N:19]=2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 6157743-Iodobenzohydrazide

Product 1

HCID 21071758HCID 21071758, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N,N-carbonyldiimidazole (800 mg, 5.0 mmol) in 5 mL of dry THF was added dropwise to an ice-cold solution of the product from Step A (1.048 g, 4.0 mmol) and triethylamine (0.60 mL, 4.0 mmol) in 12 mL of dry THF. The resultant mixture was allowed to warm to room temperature overnight, and was then concentrated under reduced pressure. The residue was partitioned between diethyl ether and water, and the ether layer was washed sequentially with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous brine, dried (magnesium sulfate), and concentrated under reduced pressure to afford a white powder. Recrystallization from ethyl acetate-hexanes afforded the title compound as a fluffy white solid. LC/MS 289.2 (M+1).

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. customThe residue was partitioned between diethyl ether and water
  3. washthe ether layer was washed sequentially with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customto afford a white powder
  7. customRecrystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-6969b2944f9e4114b04c0ee3ac839848
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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