Benzoyl chloride → HCID 18944025, compound

HRID 400305Notes

Reaction equation

HRID 400305 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH3:25])[N:21]=[C:20]([CH2:26][CH3:27])[C:19]=2[C:28]([O:30][CH3:31])=[O:29])=[CH:13][CH:12]=1)(=[O:4])=[O:3].[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.OP([O-])(O)=O.[K+]>N1C=CC=CC=1>[CH2:26]([C:20]1[C:19]([C:28]([O:30][CH3:31])=[O:29])=[C:18]([CH2:17][C:14]2[CH:13]=[CH:12][C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[S:2]([NH:1][C:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:39])(=[O:3])=[O:4])=[CH:16][CH:15]=2)[N:22]([CH2:23][CH2:24][CH3:25])[N:21]=1)[CH3:27]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516951Monobasic potassium phosphateHCID 18944016HCID 18944016, compound

Product 1

HCID 18944025HCID 18944025, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the compound obtained in example 44 (0.5 g, 1.13 mmol) in pyridine (10.8 mL) was added benzoyl chloride (0.13 mL) and the reaction mixture was stirred at room temperature under an argon atmosphere for 12 h. Then, saturated aqueous KH2PO4 (33 mL) was added and it was extracted with EtOAc. The organic phase was unwashed with 1N HCl, dried and concentrated to a crude product. This was chromatographed on silica gel (hexane-EtOAc, 1:1) to afford the title compound as a foam (0.64 g, 100%).

Workup

  1. extractionit was extracted with EtOAc
  2. customdried
  3. concentrationconcentrated to a crude product
  4. customThis was chromatographed on silica gel (hexane-EtOAc, 1:1)

Sources & evidence

ORD record
ord-f0283140e9db4213a8176cdcf928ca01
Source dataset
uspto-grants-1998_10
Patent number
US05827863

Reaction notes

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