Ammonia → HCID 11391383, compound

HRID 912729Notes

Reaction equation

HRID 912729 reaction equation
[N:1](C(OCC)=O)=NC(OCC)=O.[OH:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[CH2:19][O:18][C:17]1=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:43]1[CH:50]=[CH:49][C:46]([C:47]#[N:48])=[CH:45][CH:44]=1.N>C1(C)C=CC=CC=1.C1C=CC=CC=1.CO>[C:47]([C:46]1[CH:49]=[CH:50][C:43]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:22])[O:18][CH2:19][C:20]([NH2:1])=[O:21])=[CH:44][CH:45]=1)#[N:48]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67416823HCID 67416823, compound

Product 1

HCID 11391383HCID 11391383, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

0.61 ml (1.35 mmol) of a 2.2M solution of diethyl azodicarboxylate in toluene is added dropwise to a solution of 0.13 g (0.88 mmol) of 3-(2-hydroxyethyl)-1,3-oxazolidine-2,4-dione, prepared in Step 2.1., 0.35 g (1.35 mmol) of triphenylphosphine and 0.10 g (0.89 mmol) of 4-hydroxybenzonitrile in 2 ml of benzene, cooled using an ice bath. The reaction mixture is subsequently stirred at ambient temperature for 16 hours. It is evaporated to dryness and the product is purified by chromatography on silica gel, eluting with a 99/1 then 98/2 mixture of dichloromethane and ethyl acetate. The product is taken up in 1.5 ml of a 7M solution of ammonia (10.5 mmol) in methanol. This solution is stirred for one hour. The precipitate is filtered off and washed with ethyl acetate, to give 0.035 g of white solid.

Workup

  1. customprepared in Step 2.1
  2. customIt is evaporated to dryness
  3. customthe product is purified by chromatography on silica gel
  4. washeluting with a 99/1
  5. addition98/2 mixture of dichloromethane and ethyl acetate
  6. stirringThis solution is stirred for one hour
  7. filtrationThe precipitate is filtered off
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-d730c0ecfa5e4edfbfbe9bccb50ed60c
Source dataset
uspto-grants-2011_09
Patent number
US08026258B2

Reaction notes

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