Thionyl Chloride → HCID 9863268, compound

HRID 1635107Notes

Reaction equation

HRID 1635107 reaction equation
S(Cl)(Cl)=O.[C:5]([C@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]([CH3:19])[C@H:9]1[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1)(O)=[O:6]>C1C=CC=CC=1>[O:18]=[C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]2[C:5](=[O:6])[C:21]3[C:22]([O:30][CH3:31])=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:20]=3[C:9]=2[N:10]1[CH3:19]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86758806HCID 86758806, compound

Product 1

HCID 9863268HCID 9863268, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (10 mL) was added with stirring to 12j (200 mg, 0.5 mmol). After 4 h, the reaction mixture was diluted with benzene (50 mL) and evaporated to dryness. The dark orange solid was dissolved in chloroform and ether was added to give a dark orange solid (16 mg, 10%): mp 194-195° C.; IR (neat) 2938, 1665, 1463, 1400, 1292, 1125, 1007, 976 cm−1; 1H NMR (CDCl3, 300 MHz) δ8.67 (d, 1H, J=7.8 Hz), 8.32 (d, 1H, J=8. 0 Hz), 7.68 (t, 1H, J=8.0 Hz), 7.45 (t, 1H, J=7.8 Hz), 7.04 (s, 1H), 4.09 (s, 3H), 4.06 (s, 3H), 3.97 (s, 3H), 3.89 (s, 3H); CIMS m/z (relative intensity) 352 (MH+, 100). Anal. Calcd for C20H17NO5: C, H, N.

Workup

  1. customevaporated to dryness
  2. dissolutionThe dark orange solid was dissolved in chloroform
  3. additionether was added

Sources & evidence

ORD record
ord-5efd057cd4f64d99898e087883ced9c4
Source dataset
uspto-grants-2003_01
Patent number
US06509344B1

Reaction notes

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