Thionyl Chloride → HCID 69217114, compound

HRID 2053434Notes

Reaction equation

HRID 2053434 reaction equation
O[CH2:2][CH:3]([NH:8][C:9]([C:11]1[C:12](=[O:28])[NH:13][C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:18][C:17]([Cl:27])=[CH:16][CH:15]=2)=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6].S(Cl)(Cl)=O>C(Cl)Cl>[Cl:27][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:28])[C:11]([C:9]1[O:10][CH2:2][CH:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[N:8]=1)=[C:20]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86596753HCID 86596753, compound

Product 1

HCID 69217114HCID 69217114, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid (1-hydroxymethyl-3-methylbutyl)amide (b) (30.0 mg, 0.075 mmol) in DCM (8.0 mL) was added thionyl chloride (31.0 gL, 0.40 mmol) at rt. The reaction was stirred for 0.5 h at rt, cooled to 0° C., quenched with a cold solution of NaOH (1 N), and extracted with DCM (3×10 mL). The solvent was then removed in vacuo to provide 6-chloro-3-(4-isobutyl-4,5-dihydro-oxazol-2-yl)-4-phenyl-1H-quinolin-2-one (c) (25 mg, 87%). 1H NMR (CDCl3): δ 12.60 (b s, 1 H), 7.55-7.35 (m, 7 H); 7.20 (d, 1 H), 4.40 (t, 1 H), 4.30-4.20 (m, 1 H), 3.7 (t, 1 H), 1.60-1.50 (m, 1 H), 1.20-1.00 (m, 2 H), 0.80(dd, 6 H). MS: 381.3 (M+H).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with a cold solution of NaOH (1 N)
  3. extractionextracted with DCM (3×10 mL)
  4. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-269b5ed9787448bfad200f47adefd161
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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