Ammonia → HCID 136030561, compound

HRID 978070Notes

Reaction equation

HRID 978070 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([OH:23])=[C:6]([C:8](=[N:16][CH:17]=[CH:18][CH2:19][C:20](O)=[O:21])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:7]=1.C(N1C=CN=C1)([N:27]1C=CN=C1)=O.N>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([OH:23])=[C:6]([C:8](=[N:16][CH:17]=[CH:18][CH2:19][C:20]([NH2:27])=[O:21])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 136171397HCID 136171397, compound

Product 1

HCID 136030561HCID 136030561, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3.3 g of the acid obtained in Example 1, dissolved in 100 ml of tetrahydrofuran (THF), 1.6 g of carbonyldiimidazole is added and the mixture is stirred for 2 hrs. A solution is prepared of ammonia gas in 250 ml of anhydrous THF, into which the first solution obtained is introduced slowly. The mixture is stirred for 3 h and left to stand overnight. It is evaporated to dryness under reduced pressure and the residue is distributed between 150 ml of CH2Cl2 and 100 ml of water. The organic phase is decanted, dried over MgSO4, filtered and evaporated to dryness. An oil is obtained which is purified by chromatography on silica (eluent: ethyl acetate). The 3 final fractions containing the products are dried over MgSO4. The fractions are filtered and the filtrates evaporated to dryness. One of the 3 residues obtained, a mixture of both cis (32%) and trans (68%) isomers, is recrystallised in a mixture of ether and petroleum ether.

Workup

  1. customobtained
  2. additionis introduced slowly
  3. stirringThe mixture is stirred for 3 h
  4. waitleft
  5. waitto stand overnight
  6. customIt is evaporated to dryness under reduced pressure
  7. customThe organic phase is decanted
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customAn oil is obtained which
  12. customis purified by chromatography on silica (eluent: ethyl acetate)
  13. additionThe 3 final fractions containing the products
  14. dry with materialare dried over MgSO4
  15. filtrationThe fractions are filtered
  16. customthe filtrates evaporated to dryness
  17. customOne of the 3 residues obtained
  18. additiona mixture of both cis (32%) and trans (68%) isomers
  19. customis recrystallised in a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-2ffdcca8c9394a53a6acb36f22ed8af1
Source dataset
uspto-grants-1987_05
Patent number
US04663350

Reaction notes

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