Triethylamine → HCID 57859248, compound

HRID 1188761Notes

Reaction equation

HRID 1188761 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>C1COCC1>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][S:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH3:1])[S:3][C:4]=2[CH:10]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 35830192-Methyl-1,3-benzothiazole-6-sulfonyl chloride2×

Product 1

HCID 57859248HCID 57859248, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Compound 8 (7.0 g, 28.26 mmol) in THF (70 mL), a mixture of triethylamine (7.9 mL, 56.52 mmol) and N,N-dimethylethylene-diamine (4.67 mL, 42.38 mmol) in 20 mL THF was added dropwise. The combined mixture was stirred at room temperature for 2 hours during which time TLC showed complete disappearance of Compound 8. Solvents were removed in the rotary evaporator and the residue thus obtained was partitioned between chloroform (100 mL) and water (100 mL). The organic layer was washed with water (2×100 mL), brine (1×100 mL), dried (sodium sulfate) and evaporated to provide Compound 9 as a sticky oily solid (7.1 g, 84% yield). It was used further in the synthesis without any purification. The structure of Compound 9 is given below:

Workup

  1. additionwas added dropwise
  2. customSolvents were removed in the rotary evaporator
  3. customthe residue thus obtained
  4. customwas partitioned between chloroform (100 mL) and water (100 mL)
  5. washThe organic layer was washed with water (2×100 mL), brine (1×100 mL)
  6. dry with materialdried (sodium sulfate)
  7. customevaporated

Sources & evidence

ORD record
ord-2b2474c22143451ab06ee5468f6ed874
Source dataset
uspto-grants-2014_03
Patent number
US08674102B2

Reaction notes

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