2-Methylbenzoyl chloride → HCID 53246209, compound

HRID 1172919Notes

Reaction equation

HRID 1172919 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:5]([NH:7][OH:8])=[NH:6].[CH3:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:18]([C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[CH3:21])[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 178446942HCID 178446942, compound

Product 1

HCID 53246209HCID 53246209, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 3-chloro-4-(1-ethyl-propoxy)-N-hydroxy-benzamidine (64 mg, 0.25 mmol) (prepared by General procedure B) in pyridine (1 mL) was added a solution of 2-methylbenzoyl chloride (77 mg, 0.5 mmol) in pyridine (1 mL). The mixture was heated at about 100° C. overnight. The solvent was removed under reduced pressure and the crude product was purified via SFC(CO2/pure MeOH; gradient: 5% hold for 0.5 min, ramp at 7.3% to 50% over 6.5 min, hold at 50% for 1 min) to give 3-[3-chloro-4-(1-ethyl-propoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole (16.5 mg, 18.5%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified via SFC(CO2/pure MeOH; gradient: 5% hold for 0.5 min, ramp at 7.3% to 50% over 6.5 min, hold at 50% for 1 min)

Sources & evidence

ORD record
ord-53242ce60ce142be90340d65571b5487
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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