Triphenylphosphine → HCID 22733426, compound

HRID 2084565Notes

Reaction equation

HRID 2084565 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[CH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=1O)=O)[CH2:8]2.C12(CC(NC3C=CC(O)=CC=3O)=O)CC3CC(CC(C3)C1)C2.C12CC3CC(CC(C3)C1=CC(O)=O)C2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1[S:84]SC1C=CC=CN=1.C(N(C(C)C)C(C)C)C.[OH-].OC1C=C(O)C=CC=1N>ClCCl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[CH:11][C:12]1[S:84][C:16]3[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:15]=3[N:14]=1)[CH2:8]2

Participants

9

Reactant 7

HCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 81531DiisopropylethylamineHCID 2842562(Tricyclo[3.3.1.1~3,7~]decan-2-ylidene)acetic acidHCID 22733386HCID 22733386, compoundHCID 22733406HCID 22733406, compoundHCID 22733430HCID 22733430, compound

Product 1

HCID 22733426HCID 22733426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Adamantan-2-ylidene)-N-(2,4-dihydroxyphenyl)acetamide (formula VII) 3.0 g (adamantan-2-ylidene)acetic acid (formula R3COOH), 5.91 g triphenylphosphane and 4.95 g dipyridyldisulfide, dissolved in 100 ml of dichloromethane, are stirred at room temperature overnight. To the mixture obtained, 5.13 ml of N-ethyl-diisopropylamine and 4.83 g 2,4-dihydroxyaniline hydroxide (formula V) are added and the mixture is stirred for about 24 hours, the solvent is evaporated off, the evaporation residue is dissolved in ethyl acetate and extracted with a saturated aqueous NaH2PO4 solution and brine. The organic layer is dried, the solvent is evaporated off and the residue is purified by chromatography. The title compound is obtained (m.p. 166-169°).

Workup

  1. customTo the mixture obtained
  2. stirringthe mixture is stirred for about 24 hours
  3. customthe solvent is evaporated off
  4. dissolutionthe evaporation residue is dissolved in ethyl acetate
  5. extractionextracted with a saturated aqueous NaH2PO4 solution and brine
  6. customThe organic layer is dried
  7. customthe solvent is evaporated off
  8. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-45d29ac6cdaf45a9814c272cbec6f5c4
Source dataset
uspto-grants-2004_04
Patent number
US06716865B1

Reaction notes

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