Chloroacetonitrile → HCID 67264987, compound

HRID 1685104Notes

Reaction equation

HRID 1685104 reaction equation
[NH2:1][CH:2]1[CH:6]([C:7]([O:9]C)=O)[S:5][C:4]2[C:11]3[C:16]([CH2:17][CH2:18][C:3]1=2)=[CH:15][CH:14]=[CH:13][CH:12]=3.[Cl:19][CH2:20][C:21]#[N:22]>Cl.O1CCOCC1>[Cl:19][CH2:20][C:21]1[NH:22][C:7](=[O:9])[CH:6]2[CH:2]([C:3]3[CH2:18][CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:4]=3[S:5]2)[N:1]=1

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 67264957HCID 67264957, compound

Product 1

HCID 67264987HCID 67264987, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of EXAMPLE 12D (200 mg) and 2-chloroacetonitrile in 4M hydrochloric acid in dioxane (4 mL) was heated at 65° C. for 18 hours. The mixture was cooled, filtered and the solid heated in N,N-dimethylformamide (6 mL) at 100° C. for 2 hours. The solution was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to provide 145 mg of the title compound as a white solid. 1H NMR (DMSO-d6) δ 12.85 (bs, 1H), 7.55 (m, 1H), 7.31-7.38 (m, 3H), 4.60 (s, 2H), 3.01 (t, J=7.3 Hz, 2H), 2.93-2.96 (m, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. temperatureThe solution was cooled
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9577d367c3b44e6a95bbae11f8039761
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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