Dimethyl Sulfoxide → HCID 14652261, compound

HRID 2352494Notes

Reaction equation

HRID 2352494 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:13]([CH2:21][CH3:22])[CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH2:19][OH:20])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:21]([N:13]([CH2:11][CH3:12])[CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH:19]=[O:20])[CH3:22]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14652260HCID 14652260, compound

Product 1

HCID 14652261HCID 14652261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (32 mL, 352 mmol) in methylene chloride (800 mL) under argon atmosphere at -78° C. was added dimethylsulfoxide (54.4 mL, 704 mmol) in methylene chloride (40 mL) over 15 minutes. After stirring for 5 minutes 6-diethylaminohex-4-yn-1-ol (50 g, 296 mmol) dissolved in methylene chloride (60 mL) was added dropwise over 35 minutes. After stirring 20 minutes triethylamine (224 mL, 1600 mmol) was added at -78° C. over 30 minutes and the reaction mixture was allowed to warm to room temperature. Water (400 mL) was added, the layers were separated, and the organic layer was washed with water (2×200 mL). The aqueous layer was back-extracted with methylene chloride (2×150 mL) and the combined organic extracts were washed with brine and dried (MgSO4). Removal of solvent under reduced pressure gave a quantitative yield of the product as an oil. 1H NMR (CDCl3) δ: 1.13 (t, 6H), 2.48-2.58 (m, 6H), 2.65 (q, 2H), 3.39 (d, 2H), 9.80 (s, 1H) ppm.

Workup

  1. additionwas added dropwise over 35 minutes
  2. additionwas added at -78° C. over 30 minutes
  3. customthe layers were separated
  4. washthe organic layer was washed with water (2×200 mL)
  5. extractionThe aqueous layer was back-extracted with methylene chloride (2×150 mL)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-fd47db434f504c6bb09bdaecd46dbc9f
Source dataset
uspto-grants-1989_10
Patent number
US04877779

Reaction notes

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