Benzoyl chloride → HCID 16015645, compound

HRID 1716255Notes

Reaction equation

HRID 1716255 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:11][C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16][CH2:15]3)=[O:13])=[N:7][C:6]=2[CH:24]=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC[N:36](CC)CC>C(Cl)Cl>[N:14]1([C:12](=[O:13])[CH2:11][S:10][C:8]2[S:9][C:5]3[CH:4]=[C:3]([NH:36][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:2]=[CH:24][C:6]=3[N:7]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 59467880HCID 59467880, compound

Product 1

HCID 16015645HCID 16015645, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of compound 50 (0.22 g, 0.62 mmol) in dry CH2Cl2 (6 mL) was added benzoyl chloride (0.10 mL, 0.93 mmol) followed by dropwise addition of Et3N (0.26 mL, 1.86 mmol). The reaction was stirred overnight under N2 at room temperature. The reaction mixture was poured onto ice-water, and extracted with CH2Cl2 (3×20 mL). The combined organics extracts were washed with water (2×10 mL), and saturated NaCl (2×10 mL). Dried over MgSO4 and filtered. The solvent was removed under reduced pressure, and the product was purified by column chromatography (EtOAc/hexanes 1:1) to afford 55 as a white solid (132 mg, 46%); MS m/z: 460 (M+H)+. Anal. Calcd. For, C25H21N3O2S2: C, 65.33; H, 4.61; N, 9.14; S, 13.95. Found: C, 65.08; H, 4.64; N, 8.99; S, 13.69.

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. washThe combined organics extracts were washed with water (2×10 mL), and saturated NaCl (2×10 mL)
  4. dry with materialDried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe product was purified by column chromatography (EtOAc/hexanes 1:1)

Sources & evidence

ORD record
ord-af8927bd8e2349a3b931e2671a6a0e7b
Source dataset
uspto-grants-2010_09
Patent number
US07803790B2

Reaction notes

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