1,2-Dichloroethane → HCID 57448175, compound

HRID 1667584Notes

Reaction equation

HRID 1667584 reaction equation
[CH:1]1([S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8](O)=[O:9])[CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=[N:21]C=2C=1.O.C(Cl)CCl.[OH-].[NH4+]>CN(C=O)C.C(OCC)(=O)C.C1COCC1>[CH:1]1([S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([NH2:21])=[O:9])[CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 57448174HCID 57448174, compound

Product 1

HCID 57448175HCID 57448175, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To 2B (6.30 g, 26.2 mmol) in DMF (52.5 mL) was added HOBT.H2O (4.9 g, 32.0 mmol) and EDC (5.98 g, 31.3 mmol). After stirring 1 h at rt, the reaction was cooled to 0° C. and 25% ammonium hydroxide was added. The reaction was stirred for 1.5 h and was then diluted with ethyl acetate/THF and washed with 1N HCl (2×) and 1 N NaOH (2×). The aqueous layer was back-extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to provide 2C (5 g) as a yellow solid. LC-MS: 240.08 (M+H)+.

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. stirringThe reaction was stirred for 1.5 h
  3. washwashed with 1N HCl (2×) and 1 N NaOH (2×)
  4. extractionThe aqueous layer was back-extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-76e8462bc4f44d2185b56d242a764653
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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