Oxalic Acid → HCID 23311350, compound

HRID 746045Notes

Reaction equation

HRID 746045 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:6]O.C(N(CC)CC)C.CS(Cl)(=O)=O.[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36]>C(Cl)Cl.CCOCC>[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36].[C:8]1([C:5]2([CH2:4][CH2:3][N:2]([CH3:21])[CH3:1])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13656109HCID 13656109, compound

Product 1

HCID 23311350HCID 23311350, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 14.8 g (52 mmole) 4-dimethylamino-2-(2-hydroxyphenyl)-2-phenylbutanol in 300 ml CH2Cl2 and 21.5 ml (156 mmole) triethylamine which had been cooled in an ice bath for 20 minutes was added a solution of 6 ml (78 mmole) methanesulfonyl chloride in 50 ml CH2Cl2. After the mixture was stirred 3 hours at ice bath temperature, it was diluted with 800 ml CH2Cl2, washed with 10% NaOH solution (2×125 ml) and saturated NaCl solution (125 ml), and dried over MgSO4. Filtration and evaporation gave 14.0 g of a crude oil. A solution of 5 g of this material in 15 ml CH2Cl2 was added to excess oxalic acid in Et2O. The precipitated solid was recrystallized from ethanol to give 4.2 g (63%) of crystals, m.p. 158°-160°.

Workup

  1. washwashed with 10% NaOH solution (2×125 ml) and saturated NaCl solution (125 ml)
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and evaporation
  4. customgave 14.0 g of a crude oil
  5. customThe precipitated solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-e79b18eb6fa741e081aa179e568be37f
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

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