Ammonia → HCID 86723265, compound

HRID 1846046Notes

Reaction equation

HRID 1846046 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(N1C=CN=C1)([N:18]1C=CN=C1)=O.N.C(Cl)Cl>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 431406152-Bromo-5-(ethylsulfonyl)benzoic acid

Product 1

HCID 86723265HCID 86723265, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-bromo-5-(ethylsulfonyl)benzoic acid (Preparation 73, 8.10 g, 27.6 mmol) dissolved in THF (200 mL) was added carbonyldiimidazole (8.72 g, 41.4 mmol). The reaction was left to stir for 5 minutes under nitrogen before ammonia was bubbled through the solution. A temperature rise from 22° C. to 41° C. was observed over 10 minutes. The temperature then started to fall, reaching 35° C. after 5 minutes, after which the flow of ammonia was stopped. The reaction mixture was left to stand as a saturated ammonia solution for 30 minutes before removal of the solvent under reduced pressure. The residue was partitioned between EtOAc (500 mL) and water (500 mL) and the layers separated. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure to give the crude product. Trituration with CH2Cl2 gave the title compound as a solid in 28% yield, 2.23 g. A further portion of the title compound was isolated by drying of the filtrate and further trituration, to give a further 8%, 650 mg.

Workup

  1. waitThe reaction was left
  2. customwas bubbled through the solution
  3. waitreaching 35° C. after 5 minutes
  4. waitThe reaction mixture was left
  5. customto stand as a saturated ammonia solution for 30 minutes before removal of the solvent under reduced pressure
  6. customThe residue was partitioned between EtOAc (500 mL) and water (500 mL)
  7. customthe layers separated
  8. dry with materialThe organic layer was dried over MgSO4
  9. customthe solvent removed under reduced pressure
  10. customto give the crude product

Sources & evidence

ORD record
ord-1ff6791351a14a13ac20e7c0bec34053
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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