Triethylamine → HCID 86602386, compound

HRID 1019618Notes

Reaction equation

HRID 1019618 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11][CH2:12][OH:13])=[C:4]([CH2:8][CH2:9][OH:10])[S:5][C:6]=1[Cl:7].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH2:11][CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])=[C:4]([CH2:8][CH2:9][O:10][S:22]([CH3:21])(=[O:24])=[O:23])[S:5][C:6]=1[Cl:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58256115HCID 58256115, compound

Product 1

HCID 86602386HCID 86602386, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from step (e) (1.99 g, 8.25 mmol) in CH2Cl2 (41 ml) was cooled to 0° C. and treated with triethylamine (3.4 ml, 24.7 mmol) followed by dropwise addition of methanesulfonyl chloride (1.4 ml, 18.1 mmol) over 10 min. After 45 minutes, the crude reaction was diluted with CH2Cl2 (100 ml) and washed with ice water (25 ml), 10% citric acid (2×25 ml), sat. NaHCO3 (2×25 ml) and brine (1×25 ml). The organic layer was dried (MgSO4), concentrated to 20 ml and diluted with anhydrous dioxane (76 ml). This mixture was concentrated to remove remaining CH2Cl2 and the resulting dioxane solution was carried forward to the next reaction.

Workup

  1. customthe crude reaction
  2. washwashed with ice water (25 ml), 10% citric acid (2×25 ml), sat. NaHCO3 (2×25 ml) and brine (1×25 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated to 20 ml
  5. additiondiluted with anhydrous dioxane (76 ml)
  6. concentrationThis mixture was concentrated
  7. customto remove
  8. customthe resulting dioxane solution was carried forward to the next reaction

Sources & evidence

ORD record
ord-7b255d181eda4b73bd0e792cacd8e005
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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