Benzoyl chloride → HCID 18409332, compound

HRID 993471Notes

Reaction equation

HRID 993471 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC(C=CC[C:22]2([C:35]([NH:37][CH2:38][CH2:39][CH3:40])=[O:36])[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=CC=1)([O-])=O.C([N:43]([CH2:46][CH3:47])CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[C:1]([NH:43][C:46]1[CH:47]=[CH:35][C:22]([CH2:34][CH2:29][CH2:28][CH2:27][C:22]2([C:35]([NH:37][CH2:38][CH2:39][CH3:40])=[O:36])[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:23][CH:24]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 54548524HCID 54548524, compound

Product 1

HCID 18409332HCID 18409332, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Benzoyl chloride (156 μL, 1.35 mmol) was added dropwise to a solution of Example 207 Part A compound (490 mg, 1.23 mmol) and triethylamine (257 μL, 1.85 mmol) in CH2Cl2 (4 mL) at 0° C. under argon. The reaction was stirred at 0° C. for 30 min, diluted with CH2Cl2 (20 mL) and CHCl3 (20 mL), washed with 1N KOH (2×10 mL) and water (10 mL), then dried over MgSO4. Evaporation gave a yellow solid, which was adsorbed onto silica gel (10 g), then purified by flash chromatography on silica gel (150 g) eluting with 5% EtOAc/CH2Cl2 to give a solid. The product was dried under high vacuum at 50° C. overnight to provide title compound (412 mg, 67%) as a white solid.

Workup

  1. washwashed with 1N KOH (2×10 mL) and water (10 mL)
  2. dry with materialdried over MgSO4
  3. customEvaporation
  4. customgave a yellow solid, which
  5. custompurified by flash chromatography on silica gel (150 g)
  6. washeluting with 5% EtOAc/CH2Cl2
  7. customto give a solid
  8. customThe product was dried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-0bc0063b081b4fb8a42de478d95bf767
Source dataset
uspto-grants-2002_10
Patent number
US06472414B1

Reaction notes

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