Chloroacetonitrile → HCID 136406659, compound

HRID 1685101Notes

Reaction equation

HRID 1685101 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[Cl:18][CH2:19][C:20]#[N:21]>Cl.O1CCOCC1>[Br:7][C:6]1[C:2]2[N:1]=[C:20]([CH2:19][Cl:18])[NH:21][C:14](=[O:16])[C:3]=2[S:4][C:5]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 67265060HCID 67265060, compound

Product 1

HCID 136406659HCID 136406659, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of EXAMPLE 8A (1.47 g, 4.7 mmol), chloroacetonitrile (0.43 g, 5.7 mmol) in 4N hydrochloric acid in dioxane (10 mL) was stirred overnight at ambient temperature. The solvent was removed and the residue heated in N,N-dimethylformamide (15 mL) at 110° C. for 2 hours. After cooling, the mixture was partitioned between ethyl acetate and water and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was triturated with 1:1 ethyl acetate/hexanes to give 0.98 g (59%) of the title compound. 1H NMR (DMSO-d6) δ 13.13 (s, 1H), 7.75-7.78 (m, 2H), 7.56-7.60 (m, 3H), 4.64 (s, 2H).

Workup

  1. customThe solvent was removed
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between ethyl acetate and water
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was triturated with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6682611ca4314dc6b5fe86611fdb7a12
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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