Benzoyl chloride → HCID 16015645, compound

HRID 1404939Notes

Reaction equation

HRID 1404939 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-28bc24ce90184092a0f4e1c99f748d1c
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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