4-Iodobenzoyl chloride → HCID 67180950, compound

HRID 2400213Notes

Reaction equation

HRID 2400213 reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.C([Li])CCC.[I:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C1COCC1>[I:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([O:1][CH2:2][C:3]2[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 743734-Iodobenzoyl chlorideHCID 106304823-(Hydroxymethyl)pyridin-2(1H)-one2×HCID 178418339Butyllithium

Product 1

HCID 67180950HCID 67180950, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-80 °C

Procedure

A 25 mL round bottom flask was charged with 0.209 g (1.67 mmole) of 3-(hydroxymethyl)pyridine-2(1H)-one and suspended in 15 mL of THF under the presence of argon gas. The solution was cooled to −80° C. in a methanol bath and 1.05 mL (1.68 mmol) of butyl lithium (BuLi) was added dropwise, and the solution stirred for 20 min. 0.4454 g (1.67 mmol) of 4-iodobenzoyl chloride was dissolved in 15 mL of THF, cooled to −80° C. in a methanol bath, then added dropwise into the alcohol reaction mixture. The reaction was stirred for 48 hours at −80° C. under the presence of argon gas. The reaction was then returned to room temperature and was quenched with 20 mL of water. The reaction was washed with ethyl acetate (4×20 mL), the organic layers combined, washed with Brine (3×20 mL), and finally dried over MgSO4. The solvent was removed in vacuo to produce a dull brown solid. The compound was purified by crystallization from toluene. The yield of the product was 0.0652 g (10.99% Yield). MP: 203-205° C. IR: (cm−1): 3415.21 (m, broad), υ (O—H), 3128.97 (m, broad), υ (N—H), 1720.30 (m), υ (C═O), 1613.77 (m), υ (C═C aromatic). 1H NMR (DMSO-d6, 500 MHz) δ: 5.13 (s, 2H), 6.23 (t, J=6.6 Hz, 1H), 7.40 (dd, J=4.5, 2.1 Hz, 1H), 7.59 (dd, J=4.7, 2.1 Hz, 1H), 7.74 (d, J=4.8 Hz, 2H), 7.94 (d, J=4.8 Hz, 2H), 11.78 (s, 1H). 13C NMR (DMSO-d6) δ: 165.76, 161.84, 139.75, 138.29, 135.79, 131.41, 129.58, 126.43, 105.09, 102.35, 62.81. HRMS: m/e, found 377.9583 (M+Na+). Calc. for C13H10INO3Na: 377.9603.

Workup

  1. temperaturecooled to −80° C. in a methanol bath
  2. stirringThe reaction was stirred for 48 hours at −80° C. under the presence of argon gas
  3. customwas then returned to room temperature
  4. customwas quenched with 20 mL of water
  5. washThe reaction was washed with ethyl acetate (4×20 mL)
  6. washwashed with Brine (3×20 mL)
  7. dry with materialfinally dried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customto produce a dull brown solid
  10. customThe compound was purified by crystallization from toluene

Sources & evidence

ORD record
ord-904effcdbc7348dbaf6c560e9cbbd11d
Source dataset
uspto-grants-2014_08
Patent number
US08795630B2

Reaction notes

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