Nitrogen → HCID 66928550, compound

HRID 42810Notes

Reaction equation

HRID 42810 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:13][CH:12]=[C:11]([CH2:14]O)[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.S([Cl:27])(C)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:27][CH2:14][C:11]1[CH:10]=[C:9]([C:4]2([CH3:3])[O:8][CH2:7][CH2:6][O:5]2)[S:13][CH:12]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66928500HCID 66928500, compound

Product 1

HCID 66928550HCID 66928550, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-3-yl]-methanol (460 mg, 2.30 mmol) in dry CH2Cl2 (4.6 mL) was treated at 0° C. with Et3N (0.42 mL, 2.99 mmol) followed by DMAP (28 mg, 0.23 mmol) and Ms-Cl (0.21 mL, 2.76 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (20 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a pale yellow oil. TLC:rf (1:4 EA-Hept)=0.35.

Workup

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with CH2Cl2 (20 mL)
  3. dry with materialextracts were dried over NaSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hept-EA)

Sources & evidence

ORD record
ord-efc475add29548edbd361e787547b8d9
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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