Morpholine → HCID 68573055, compound

HRID 1189722Notes

Reaction equation

HRID 1189722 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7](Cl)=[O:8])[S:5][CH:6]=1.CC[N:12](C(C)C)C(C)C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:12][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:8])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 27954834-Bromo-2-Thiophenecarbonyl Chloride

Product 1

HCID 68573055HCID 68573055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-thiophenecarbonyl chloride (1.0 g, 4.4 mmol) in DCM (10 ml) cooled to 0° C. was added DIPEA (0.85 ml, 4.8 mmol) and morpholine (0.4 g, 4.6 mmol) dropwise. Stirring was continued until complete consumption of the starting material was observed by LC-MS. The reaction was quenched by the addition of water, which was washed with further portions of 2N HCl, dried over sodium sulfate, filtered and concentrated in vacuo to yield the desired compound without need for further purification (1.2 g, 100%). δH (500 MHz, CHLOROFORM-d) 7.38 (1H, s), 7.18 (1H, s), 3.63-3.83 (8H, m); TR=1.52 min.

Workup

  1. customwas continued until complete consumption of the starting material
  2. customThe reaction was quenched by the addition of water, which
  3. washwas washed with further portions of 2N HCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5216b2e6bc744b1e94027d7b7a6e14c2
Source dataset
uspto-grants-2014_03
Patent number
US08674132B2

Reaction notes

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