Hydrochloric Acid → HCID 178438307, compound

HRID 247605Notes

Reaction equation

HRID 247605 reaction equation
[OH:1][CH2:2][CH2:3][N:4]=[C:5]([CH:7]1[CH:12]([C:13]([OH:15])=[O:14])[CH:11]2[CH2:16][C:8]1([CH2:17][CH:18]=[CH2:19])[CH:9]=[CH:10]2)[OH:6].C(N(CC)CC)C.[S:27](Cl)([OH:30])(=O)=[O:28].[CH4:32].Cl>C1(C)C=CC=CC=1>[CH3:32][S:27]([O:1][CH2:2][CH2:3][N:4]=[C:5]([CH:7]1[CH:12]([C:13]([OH:15])=[O:14])[CH:11]2[CH2:16][C:8]1([CH2:17][CH:18]=[CH2:19])[CH:9]=[CH:10]2)[OH:6])(=[O:30])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 19821184Methane sulfochlorideHCID 178438304HCID 178438304, compound

Product 1

HCID 178438307HCID 178438307, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

49.26 g of allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid N-(2'-hydroxyethyl)imide (prepared according to Example 3a) and 22.26 g of triethylamine are dissolved in 160 g of toluene, and the solution is cooled under nitrogen to 5° C. With stirring, 22.91 g of methane sulfochloride are added dropwise for 1 hour, while keeping the temperature in the range from 5° to 10° C. by external cooling. The mixture is subsequently stirred for a further 18 hours at room temperature. The pH is adjusted with 1N HCl to 5 and the mixture is washed with water and dried. The product is isolated as described in Example 7. Yield: 54 g (83.0% of theory); η40°C. =2138.4 mPa.s; n25D =1.5238.

Workup

  1. customfrom 5° to 10° C.
  2. stirringThe mixture is subsequently stirred for a further 18 hours at room temperature
  3. washthe mixture is washed with water
  4. customdried
  5. customThe product is isolated

Sources & evidence

ORD record
ord-d9088bb0c9484be2b6d6bc4325b58c02
Source dataset
uspto-grants-1987_11
Patent number
US04709047

Reaction notes

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