Triethylamine → HCID 21487793, compound

HRID 1414532Notes

Reaction equation

HRID 1414532 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[C:21]2[S:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:22][CH3:23])[C:13]([CH2:27][CH2:28][OH:29])([CH2:24][CH2:25][OH:26])[C:12]=2[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:23][O:22][C:18]1[C:19]2[S:20][C:21]3[C:12](=[CH:11][CH:10]=[CH:9][C:8]=3[O:7][CH3:6])[C:13]([CH2:24][CH2:25][O:26][S:2]([CH3:1])(=[O:4])=[O:3])([CH2:27][CH2:28][O:29][S:2]([CH3:1])(=[O:4])=[O:3])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21487805HCID 21487805, compound

Product 1

HCID 21487793HCID 21487793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulphonyl chloride (1.71 ml.) is added dropwise over 5 minutes at 5° C. to a solution of 4,5-dimethoxy-9,9-bis(2'-hydroxyethyl)thioxanthene (3.46 g.), and triethylamine (4.18 ml.) in dry methylene chloride (70 ml.) with stirring. The mixture is stirred for 15 minutes, diluted with methylene chloride (70 ml.) and washed successively with water, 10% aqueous HCl, a saturated solution of NaHCO3 and brine. The solution is dried over MgSO4 and evaporated to dryness. The solid residue is recrystallised from ethanol to give 4,5-dimethoxy-9,9-bis(2'-methanesulphonyloxyethyl)thioxanthene, m.p. 176°-178° C.

Workup

  1. stirringThe mixture is stirred for 15 minutes
  2. washwashed successively with water, 10% aqueous HCl
  3. dry with materialThe solution is dried over MgSO4
  4. customevaporated to dryness
  5. customThe solid residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-912465394a5e402fa5f05f991c957ac2
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

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