Triethylamine → HCID 86607171, compound

HRID 602519Notes

Reaction equation

HRID 602519 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]([CH3:17])[C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]([CH3:17])[C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:25](=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29])=[C:11]([CH3:16])[CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 61438572HCID 61438572, compound

Product 1

HCID 86607171HCID 86607171, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N(4)-(5-Chloro-thiophen-2-ylmethyl)-2,N(4)-dimethyl-benzene-1,4-diamine (54 mg, 0.20 mmol) and triethylamine (84 μL, 0.60 mmol) in dry tetrahydrofuran (1 mL) was added pentanoyl chloride (36 μL, 0.30 mmol), and the mixture was stirred for 1 hour at room temperature after which it was partitioned between saturated aqueous sodium bicarbonate (5 mL) and ethyl acetate (5 mL). The organic layer was dried over sodium sulfate, volatiles were evaporated, and the residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures) to yield the title compound as a white solid (61 mg, 86%).

Workup

  1. customwas partitioned between saturated aqueous sodium bicarbonate (5 mL) and ethyl acetate (5 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate, volatiles
  3. customwere evaporated
  4. customthe residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-48130343923d4ecab6475235e798ca94
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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