Triethylamine → HCID 178513788, compound

HRID 2427969Notes

Reaction equation

HRID 2427969 reaction equation
[NH2:1]/[C:2](/[C:17]#[N:18])=[C:3](\[NH:6][C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1)=[O:8])/[C:4]#[N:5].O[C@H]1C[CH2:24][C@H:23]([C:26](O)=O)[CH2:22][CH2:21]1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.[O-][Mn](=O)(=O)=O.[K+].N/C(/C#N)=C(\N)/C#N.C([O:70][CH2:71][CH3:72])(=O)C>C1(C)C=CC=CC=1.C(#N)C>[OH:16][C@H:13]1[CH2:14][CH2:15][C@H:10]([N:9]2[C:7](=[O:8])[NH:6][C:3]3[C:4]2=[N:5][C:26]([C:23]2[CH:22]=[CH:21][CH:72]=[C:71]([OH:70])[CH:24]=2)=[N:1][C:2]=3[C:17]([NH2:18])=[O:43])[CH2:11][CH2:12]1

Participants

10

Reactant 7

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 516875Potassium PermanganateHCID 2723951DiaminomaleonitrileHCID 178511349HCID 178511349, compoundHCID 178525780HCID 178525780, compound

Product 1

HCID 178513788HCID 178513788, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

1-((Z)-2-Amino-1,2-dicyanovinyl)-3-(trans-4-hydroxycyclohexyl)urea. Trans-4-hydroxycyclohexane carboxylic acid (3.0 g, 20.80 mmol), triethylamine (2.10 g, 20.80 mmol) and diphenylphosphorylazide (5.72 g, 20.80 mmol) were combined in toluene and stirred at room temperature. The reaction was monitored via thin layer chromatography (50% ethyl acetate in hexanes, KMnO4 stain). After 30 min, the solution was condensed under reduced pressure and the oil diluted with acetonitrile (30 mL) followed by the addition of diaminomaleonitrile (2.24 g, 21.84 mmol). The solution was heated to 65° C. for 16 h. The resultant heterogeneous mixture was triturated with water. The resultant precipitate was filtered and dried under vacuum to afford the title compound (1.60 g, 31%). MS (ESI) m/z 250.1[M+1]+.

Workup

  1. customcondensed under reduced pressure
  2. temperatureThe solution was heated to 65° C. for 16 h
  3. customThe resultant heterogeneous mixture was triturated with water
  4. filtrationThe resultant precipitate was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5f02fa238aff4c7e8a428447630106c7
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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