Acetic Acid → HCID 22504152, compound

HRID 1814310Notes

Reaction equation

HRID 1814310 reaction equation
C(O)(=O)C.[Cl-:5].[Li+].[S:7](=[O:9])=[O:8].F[B-](F)(F)F.[N+](=[C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][CH:18]1[O:26][CH2:27][CH2:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)=[N-]>O1CCOCC1.C(#N)C.[Cu]Cl>[Cl:5][S:7]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][C:18]=1[O:26][CH2:27][CH2:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)(=[O:9])=[O:8]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 1119Sulfur Dioxide2×HCID 433294Lithium ChlorideHCID 86588212HCID 86588212, compound

Product 1

HCID 22504152HCID 22504152, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of acetic acid (8 mL) and dioxane (8 mL) at 0° C. was added lithium chloride (0.36 g, 8.46 mmol) and copper (I) chloride (0.042 g, 0.42 mmol). Sulfur dioxide (40 mL) was then condensed into this mixture by means of a cold finger at −78° C. A solution of 4-diazo-3-(2-naphthalen-1-yl-ethoxy)-benzamide fluoroborate in dioxane (20 mL) and acetonitrile (5 mL) was added in one portion to the sulfur dioxide mixture. The reaction was stirred at 0° C. for 3 hours and then heated to 65° C. overnight. The reaction was then cooled to room temperature and poured onto ethyl acetate (500 mL) and washed with water (50 mL), 1N sodium hydroxide (50 mL), saturated sodium bicarbonate (50 mL), and saturated sodium chloride (50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 4-(chlorosulfonyl)-3-(2-naphthalen-1-yl-ethoxy)-benzamide as an orange oil. 1HNMR(300 MHz, CDCl3) 8.00 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.68 (d, 1H), 7.57 (s, 1H), 7.40 (m, 4H), 6.21 (bs, 1H), 4.49 (t, 2H), 3.64 (t, 2H).

Workup

  1. customcondensed into this mixture by means of a cold finger at −78° C
  2. temperatureheated to 65° C. overnight
  3. temperatureThe reaction was then cooled to room temperature
  4. additionpoured onto ethyl acetate (500 mL)
  5. washwashed with water (50 mL), 1N sodium hydroxide (50 mL), saturated sodium bicarbonate (50 mL), and saturated sodium chloride (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58b5b818c6ec4544a3198c515324b14a
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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