4-Methoxyphenol → HCID 14349037, compound

HRID 346065Notes

Reaction equation

HRID 346065 reaction equation
[OH:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:3]1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([O:1][CH:2]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6][CH2:5][N:4]([S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:15])=[O:14])[CH2:3]2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 90154-MethoxyphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12434915HCID 12434915, compound

Product 1

HCID 14349037HCID 14349037, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 1-hydroxy-2,3,4,5-tetrahydro-3-(p-toluenesulfonyl)-3-benzazepine (15 g, 47 mmole), p-methoxyphenol (7 g, 57 mmole) and triphenylphosphine (57 mmole) in 300 ml benzene, cooled with an ice bath, was slowly dropped a solution of diethyl azodicarboxylate (10 g, 57 mmole) in 100 ml benzene. After stirring two hours at ambient temperature, the reaction mixture was filtered to remove sym-dicarbethoxyhydrazine (8 g, 96%, m.p. 130°-132° C.), then evaporated to an oil which was purified by column chromatography (silica gel, dichloromethane) to give an oil. This oil was crystallized from hexane-ether to give 6 g (30%) of 1-(p-methoxyphenoxy)-2,3,4,5-tetrahydro-3-(p-toluenesulfonyl)-3-benzazepine, m.p. 84°-85° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove sym-dicarbethoxyhydrazine (8 g, 96%, m.p. 130°-132° C.)
  3. customevaporated to an oil which
  4. customwas purified by column chromatography (silica gel, dichloromethane)
  5. customto give an oil
  6. customThis oil was crystallized from hexane-ether

Sources & evidence

ORD record
ord-f94ab60b064e42b983cb89cacb3160cf
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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