4-Nitrophenol → HCID 131709884, compound

HRID 1579154Notes

Reaction equation

HRID 1579154 reaction equation
[CH2:1]([S:3][C:4]1[CH:23]=[CH:22][C:7]2[N:8]([CH3:21])[C:9]3[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=3[CH:11]=C(CC(O)=O)[C:6]=2[CH:5]=1)[CH3:2].[CH:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[C:26]([OH:33])[CH:25]=1.[CH:34]1(N=C=NC2CCCCC2)CCCCC1.[C:49](OCC)(=[O:51])[CH3:50]>>[CH2:1]([S:3][C:4]1[CH:23]=[CH:22][C:7]2[N:8]([CH3:21])[C:9]3[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=3[CH:11]=[C:50]([C:49]([O:33][C:26]3[CH:27]=[CH:28][C:29]([N+:30]([O-:32])=[O:31])=[CH:24][CH:25]=3)=[O:51])[C:6]=2[C:5]=1[CH3:34])[CH3:2]

Participants

5

Reactant 4

HCID 9804-NitrophenolHCID 8857Ethyl Acetate2×HCID 10868Dicyclohexylcarbodiimide2×HCID 12813984HCID 12813984, compound

Product 1

HCID 131709884HCID 131709884, compound

Procedure

A suspension of 2 g of 2-ethylthio-5-methyl-11-carboxymethyl [5H] dibenzo (b,f) azepine in 40 ml of ethyl acetate was heated until dissolution occured and after cooling the mixture, 840 mg of p-nitrophenol were added thereto. After total dissolution, 1.28 g of dicyclohexylcarbodiimide in 4.8 ml of ethyl acetate were added thereto and the mixture was refluxed with stirring for 1 hour. 130 mg of dicyclohexylcarbodiimide were then added and reflux with stirring was continued for 30 minutes. After cooling, the mixture was vacuum filtered and the filtrate was distilled to dryness under reduced pressure to obtain 3.9 g of raw product. The product was purified by chromatography over silica gel with a 98-2 benzene-ethyl acetate mixture as eluant to obtain 2.4 g of 2-ethylthio-5-methyl-11-(p-nitrophenoxycarbonyl)-methyl [5H] dibenzo (b,f) azepine as a yellow oil soluble in ethyl acetate, ethanol and chloroform and insoluble in water.

Workup

  1. temperaturewas heated until dissolution
  2. additionwere added
  3. additionwere added
  4. temperaturethe mixture was refluxed
  5. temperaturereflux
  6. stirringwith stirring
  7. waitwas continued for 30 minutes
  8. temperatureAfter cooling
  9. filtrationfiltered
  10. distillationthe filtrate was distilled to dryness under reduced pressure
  11. customto obtain 3.9 g of raw product
  12. customThe product was purified by chromatography over silica gel with a 98-2 benzene-ethyl acetate mixture as eluant

Sources & evidence

ORD record
ord-f2aaa3005c344dd89005c7aa08831535
Source dataset
uspto-grants-1976_01
Patent number
US03931151

Reaction notes

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