Phloroglucinol → HCID 9968839, compound

HRID 1107660Notes

Reaction equation

HRID 1107660 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([CH:14]=[C:12]([OH:13])[CH:11]=[C:9]([OH:10])[CH:8]=1)[OH:7].CN1CCOCC1>O1CCCC1>[CH3:1][S:2]([O:7][C:6]1[CH:14]=[C:12]([O:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[C:9]([O:10][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 359PhloroglucinolHCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chloride

Product 1

HCID 9968839HCID 9968839, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

39.8 g (0.33 mol) of methanesulfonic acid chloride were added dropwise at 0° C. within the course of 30 minutes to a solution of 12.6 g (0.10 mol) of phloroglucinol and 101 g (1.0 mol) of N-methylmorpholine in 200 ml of dry tetrahydrofuran in such a way that the temperature did not rise above 10° C. After the dropwise addition, the ice bath was removed, and the mixture was warmed to room temperature and stirred for 2 hours at this temperature. The mixture was then slowly added dropwise with continuous stirring to 3 l of ice water, and the resulting precipitate was filtered off with suction and washed until neutral with water. After drying, this gave 32.9 g (91%) of a colorless powder of melting point 145 to 149° C. Recrystallization from an isopropanol/acetone solvent mixture gave colorless, highly light-refracting platelets of melting point 150° C.

Workup

  1. customdid not rise above 10° C
  2. additionAfter the dropwise addition
  3. customthe ice bath was removed
  4. additionThe mixture was then slowly added dropwise
  5. stirringwith continuous stirring to 3 l of ice water
  6. filtrationthe resulting precipitate was filtered off with suction
  7. washwashed until neutral with water
  8. customAfter drying
  9. customRecrystallization from an isopropanol/acetone solvent mixture
  10. customgave colorless

Sources & evidence

ORD record
ord-50d03132b6b5420d8e469d06713a9576
Source dataset
uspto-grants-2000_05
Patent number
US06063545

Reaction notes

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