Triethylamine → HCID 178513788, compound

HRID 391634Notes

Reaction equation

HRID 391634 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-5cf6fa8390ca4ad6be9243863a57f80b
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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