Triethylamine → HCID 21445734, compound

HRID 597592Notes

Reaction equation

HRID 597592 reaction equation
[CH3:1][NH:2][S:3](Cl)(=[O:5])=[O:4].[CH3:7][C:8]1([CH3:24])[C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[O:10][CH:9]1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C>O1CCCC1>[CH3:1][NH:2][S:3]([O:17][C:14]1[CH:15]=[CH:16][C:11]2[O:10][CH:9]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:8]([CH3:24])([CH3:7])[C:12]=2[CH:13]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28012795-Benzofuranol, 2,3-dihydro-3,3-dimethyl-2-(4-morpholinyl)-HCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 21445734HCID 21445734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° to 5°C and while stirring, 36 parts (by weight) of methylaminosulfonyl chloride was added to a solution of 48.8 parts of 2,3-dihydro-3,3-dimethyl-2-morpholino-5-hydroxybenzofuran and 27.3 parts of triethylamine in 130 parts of tetrahydrofuran. The reaction mixture was stirred for 1 hour at room temperature and then filtered. The filtrate was concentrated in vacuo and the residue dissolved in 250 parts of methanol. After addition of 100 parts of water and treatment of the solution with activated carbon, crystallization was initiated by cooling. The mush of crystals was suction filtered, washed with 50wt% aqueous methanol and dried in vacuo. The crude product melted at 125° to 128°C. Pure 2,3-dihydro-3,3-dimethyl-2-morpholinobenzofuran-5-yl methylaminosulfonate was obtained by recrystallizing a sample from 80% methanol.

Workup

  1. stirringThe reaction mixture was stirred for 1 hour at room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue dissolved in 250 parts of methanol
  5. additionAfter addition of 100 parts of water and treatment of the solution
  6. customwith activated carbon, crystallization
  7. temperatureby cooling
  8. filtrationfiltered
  9. washwashed with 50wt% aqueous methanol
  10. customdried in vacuo

Sources & evidence

ORD record
ord-9f83f1fcc89a46eebcf37073cff2bcb8
Source dataset
uspto-grants-1977_03
Patent number
US04014904

Reaction notes

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