Ethane, 1,2-dichloro-1-ethoxy- → HCID 66659136, compound

HRID 420510Notes

Reaction equation

HRID 420510 reaction equation
[NH2:1][C:2]1[C:3]([Cl:18])=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:8][N:9]=1)[C:5]#[N:6].Cl[CH:20](OCC)[CH2:21]Cl>CCOC(C)=O>[Cl:18][C:3]1[C:2]2[N:9]([CH:20]=[CH:21][N:1]=2)[CH:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:4]=1[C:5]#[N:6]

Participants

4

Reactant 2

HCID 79077Ethane, 1,2-dichloro-1-ethoxy-HCID 451233402-Amino-3-chloro-5-(2,4-dichloro-phenyl)-isonicotinonitrile

Product 1

HCID 66659136HCID 66659136, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

In a sealed tube, a mixture of 2-amino-3-chloro-5-(2,4-dichloro-phenyl)-isonicotinonitrile (285 mg, 0.96 mmol) and 1,2-dichloro-1-ethoxy-ethane (0.64 mL, 5.25 mmol) was heated at 150° C. for 17 min under microwave irradiation. The reaction mixture was cooled to RT, poured into AcOEt (75 mL) and washed with a 2.0 M Na2CO3 solution in water (2×25 mL). The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→3:7) to yield the title compound (185 mg, 0.57 mmol, 60%) as a brownish solid. MS: 322 [M+1]+; HPLC: AtRet=2.17; TLC: RF 0.13 (hexane/DCM/TBME 1:1:2).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with a 2.0 M Na2CO3 solution in water (2×25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→3:7)

Sources & evidence

ORD record
ord-3472f67393b54121b315b14f0b5c20a6
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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