Sodium Hydroxide → HCID 59164408, compound

HRID 1441563Notes

Reaction equation

HRID 1441563 reaction equation
[CH3:1][S:2]([NH:5][NH2:6])(=[O:4])=[O:3].C[O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([C:16](=[O:21])[CH2:17][CH2:18][O:19][CH3:20])[C:13]([C:22]([F:25])([F:24])[F:23])=[CH:12][C:11]=1[N:26]=[C:27]=[O:28].[OH-].[Na+]>C1COCC1>[CH3:20][O:19][CH2:18][CH2:17][C:16]([C:14]1[CH:15]=[C:10]2[C:11](=[CH:12][C:13]=1[C:22]([F:23])([F:24])[F:25])[NH:26][C:27](=[O:28])[N:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:9]2=[O:8])=[O:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 269268MethanesulfonohydrazideHCID 11965697HCID 11965697, compound

Product 1

HCID 59164408HCID 59164408, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of CH3SO2NHNH2 (61 mg, 0.555 mmol) in THF (1 mL) was slowly added dropwise to a solution of 2-isocyanato-5-(3-methoxy-propionyl)-4-trifluoromethyl-benzoic acid methyl ester (167 mg, 0.505 mmol) in dry THF (2.6 mL). After stirring the mixture at r.t. for 105 min, aq NaOH (1 M, 0.53 mL) was added and stirring was continued for 60 min. The reaction mixture was concentrated and the residue was taken in EtOAc and washed with water. The aqueous phase was extracted with EtOAc (3×), all organic phases are combined, washed with brine and dried (Na2SO4) and the solvent was evaporated to dryness yielding the title compound (194 mg, 94%) as a white powder, mp 186-191° C.

Workup

  1. stirringstirring
  2. waitwas continued for 60 min
  3. concentrationThe reaction mixture was concentrated
  4. washwashed with water
  5. extractionThe aqueous phase was extracted with EtOAc (3×)
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-5c088747ff0248c8a3be1f406471befb
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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