Ethanolamine → HCID 20496657, compound

HRID 1074416Notes

Reaction equation

HRID 1074416 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:44]=[CH:43][C:24]([C:25]([N:27]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=3)[C:29]([CH2:38][C:39]([OH:41])=O)=[C:28]2[CH3:42])=[O:26])=[CH:23][CH:22]=1.[CH2:45]([CH2:47][NH2:48])O.C(N(CC)CC)C>C(#N)C.C(Cl)(Cl)(Cl)Cl>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([N:27]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=3)[C:29]([CH2:38][C:39]3[O:41][CH2:45][CH2:47][N:48]=3)=[C:28]2[CH3:42])=[O:26])=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 3715IndomethacinHCID 8471TriethylamineHCID 11776Triphenylphosphine

Product 1

HCID 20496657HCID 20496657, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 3.93 g of triphenylphosphine in 80 ml of absolute acetonitrile was added dropwise under stirring at 25° C. under argon to a solution of 1.789 g of 1-p-chlorobenzoyl-2-methyl-5-methoxyindol-3-acetic acid, 0.305 g of ethanolamine, 2.02 g of triethylamine, and 3.176 g of carbon tetrachloride in 100 ml of absolute acetonitrile, for a period of three and a half hours. After 18 hours at 24° C., the mixture was evaporated under vacuum and the crystalline residue agitated with 200 ml of ethyl ether and 75 ml of 2 N aqueous sodium hydroxide solution. After separation of the aqueous phase and secondary extraction with three times 40 ml of ethyl ether, the combined ether extracts were dried (Na2SO4) and concentrated, during which step triphenylphosphine oxide was crystallized. The filtrate was evaporated and chromatographed with toluene on 210 g of aluminum oxide, activity stage IV (alkaline; Woelm); after a forerun of 300 ml, the subsequent 800 ml of eluate yielded 1.38g of a light-yellow, oily (4-chlorophenyl)-[5-methoxy-2-methyl-3-(oxazolin-2-ylmethyl)-1-indolyl]ketone.

Workup

  1. customthe mixture was evaporated under vacuum
  2. customAfter separation of the aqueous phase and secondary extraction with three times 40 ml of ethyl ether
  3. dry with materialthe combined ether extracts were dried (Na2SO4)
  4. concentrationconcentrated, during which step triphenylphosphine oxide
  5. customwas crystallized
  6. customThe filtrate was evaporated
  7. customchromatographed with toluene on 210 g of aluminum oxide, activity stage IV (alkaline; Woelm)

Sources & evidence

ORD record
ord-9fcc3047c3f44b039fea101323f7213a
Source dataset
uspto-grants-1983_07
Patent number
US04391814

Reaction notes

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