Benzoyl chloride → HCID 334017, compound

HRID 1637903Notes

Reaction equation

HRID 1637903 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[N:8][CH2:9][C:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.[Na+].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:16]([N:8]1[CH2:9][C:10](=[O:12])[O:11][CH:7]1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 23663841HCID 23663841, compound

Product 1

HCID 334017HCID 334017, compound

Procedure

(R/S)-N-Benzoyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one (21) was prepared from sodium N-(para-methoxybenzylidene)-glycinate (2.15 g, 10.0 mM) and benzoyl chloride (1.16 mL, 10.0 mM) following general procedure D and obtained as a white solid after purification by flash column chromatography, using 20% ethyl acetate/petrol as eluant (2.08 g, 70%): mp 130-132° C.; IR (KBr): 1795, 1635 cm-1 ; 1H NMR (200 MHz, CDCl3): δ 6.84-7.55 (m, 10H), 4.35 (br, 2H), 3.78 (s, 3H); 13C NMR (50.3 MHz, CDCl3): 169.4, 169.3, 160.6, 133.6, 131.6, 128.6, 128.3, 127.7, 127.5, 114.3, 89.9, 55.4, 46.7; LRMS (EI): 298 (MH+). Anal. Calcd for C17H15NO4 : C, 68.68; H, 5.05; N, 4.71; found: C, 68.62; H, 5.01; N, 4.57.

Workup

  1. customobtained as a white solid
  2. customafter purification by flash column chromatography

Sources & evidence

ORD record
ord-4ea0634532bd470eaf10ea8ffb8211b0
Source dataset
uspto-grants-2000_03
Patent number
US06043278

Reaction notes

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