Ammonium Chloride → HCID 21293761, compound

HRID 622103Notes

Reaction equation

HRID 622103 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[CH:8]1[C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][C:12]=2[CH:11]=[C:10]([CH:21]([NH:23][OH:24])[CH3:22])[CH:9]=1.[NH4+].[Cl-]>C1COCC1>[OH:24][N:23]([CH:21]([C:10]1[CH:9]=[CH:8][C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][C:12]=2[CH:11]=1)[CH3:22])[C:6]([NH2:5])=[O:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 70696Trimethylsilyl isocyanateHCID 21245315HCID 21245315, compound

Product 1

HCID 21293761HCID 21293761, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Trimethylsilyl isocyanate (1.2 mL) was added to a solution of 1-(3-dibenzofuranyl)ethyl hydroxylamine (0.88 g, 3.87 mmole), prepared as described in example 1, step c, in THF (6 mL). The mixture was heated at 60° C. for one hour and then poured into saturated NH4Cl solution. This was extracted with ethyl acetate (3×100 mL). The organic layer was concentrated in vacuo and the residue was triturated with ether to give the desired product as a white solid (0.84 g, 80%). (R1 =NH2, A=CHCH3 --, X=0, Y=H)

Workup

  1. customprepared
  2. extractionThis was extracted with ethyl acetate (3×100 mL)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-ea9d1ca2a6ec4e5badb1276a57cf8a8e
Source dataset
uspto-grants-1988_09
Patent number
US04769387

Reaction notes

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