Acetonitrile → HCID 58182736, compound

HRID 1361479Notes

Reaction equation

HRID 1361479 reaction equation
[Cl:1][C:2]1[N:6]=[C:5](Cl)[S:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C([O-])([O-])=O.[K+].[K+].CC#N>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:6]=[C:5]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH3:8])[S:4][N:3]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 58182736HCID 58182736, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3,5-dichloro-1,2,4-thiadiazole (0.14 g, 0.93 mmol), 2-methoxyphenylboronic acid (0.16 g, 1.0 mmol), Pd(PPh3)4 (11 mg, 9.3 mmol), K2CO3 (0.26 g, 1.9 mmol), and CH3CN (3 mL containing 10% H2O) was sealed in a microwave vessel and heated by microwave irradiation at 100° C. for three minutes. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield 3-chloro-5-(2-methoxyphenyl)-1,2,4-thiadiazole. LC/MS: m/z 227 (M+H)+ at 3.45 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas sealed in a microwave vessel
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72d88bdc658c4ac2a556166029f81446
Source dataset
uspto-grants-2011_02
Patent number
US07880008B2

Reaction notes

Loading…