Ammonia → HCID 69792683, compound

HRID 988041Notes

Reaction equation

HRID 988041 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([C:24]2[CH:25]=[C:26]([CH:32]=[CH:33][C:34]([O:36]CC)=[O:35])[CH:27]=[CH:28][C:29]=2[O:30][CH3:31])=[CH:12][C:13]2[C:14]([CH3:23])([CH3:22])[CH2:15][CH2:16][C:17]([CH3:21])([CH3:20])[C:18]=2[CH:19]=1)(O)=[O:2].C1([NH:45]C2CCCCC2)CCCCC1.S(Cl)(Cl)=O.C(N(CC)CC)C.N.Cl>ClCCl.C(OCC)C.C1COCC1.O>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([C:24]2[CH:25]=[C:26]([CH:32]=[CH:33][C:34]([OH:36])=[O:35])[CH:27]=[CH:28][C:29]=2[O:30][CH3:31])=[CH:12][C:13]2[C:14]([CH3:23])([CH3:22])[CH2:15][CH2:16][C:17]([CH3:21])([CH3:20])[C:18]=2[CH:19]=1)(=[O:2])[NH2:45]

Participants

11

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 7582DicyclohexylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 69792533HCID 69792533, compound

Product 1

HCID 69792683HCID 69792683, compoundYield 62.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.27 g (2.43 mmol) of ethyl 3-{3-[3-(5-carboxypentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylate obtained in Example 24(a) dissolved in 35 ml of dichloromethane was introduced into a round-bottomed flask, 505 μl (2.55 mmol) of dicyclohexylamine were added, and the mixture was stirred for 10 minutes. Then 186 μl (2.55 mmol) of thionyl chloride were added dropwise and the mixture was stirred at room temperature for 10 minutes. The reaction medium was evaporated to dryness, the residue obtained was taken up in ethyl ether, the suspension was filtered and the filtrate was evaporated. The residue obtained was dissolved in 15 ml of THF and the solution was introduced dropwise under nitrogen into a three-necked flask containing 20 ml of THF, 405 μl (2.92 mmol) of triethylamine and 160 μl of a 34% aqueous ammonia solution (2.67 mmol). The mixture was stirred at room temperature for 30 minutes, the reaction medium was poured into water, acidified to a pH of 1 with 1N hydrochloric acid and extracted with ethyl ether, and the organic phase was decanted, dried over magnesium sulfate, filtered and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of heptane and ethyl acetate (80:20). After evaporation of the solvents, 750 mg (60%) of the expected compound were obtained in the form of a white powder having a melting point of 133°-135° C.

Workup

  1. additionwas introduced into a round-bottomed flask
  2. stirringthe mixture was stirred at room temperature for 10 minutes
  3. customThe reaction medium was evaporated to dryness
  4. customthe residue obtained
  5. filtrationthe suspension was filtered
  6. customthe filtrate was evaporated
  7. customThe residue obtained
  8. additionthe solution was introduced dropwise under nitrogen into a three-necked flask
  9. stirringThe mixture was stirred at room temperature for 30 minutes
  10. extractionextracted with ethyl ether
  11. customthe organic phase was decanted
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated
  15. customThe residue obtained
  16. customwas purified by chromatography on a silica column
  17. washeluted with a mixture of heptane and ethyl acetate (80:20)
  18. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-471cc00f650c4501a00d7d4f73413d24
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

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