Triethylamine → HCID 24960299, compound

HRID 2092507Notes

Reaction equation

HRID 2092507 reaction equation
[F:1][C@@:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[CH:9][CH:8]=1)([CH3:6])[C:3](O)=[O:4].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:33][S:34]([NH2:37])(=[O:36])=[O:35].C(N(CC)CC)C>C(Cl)Cl>[F:18][C:17]([F:20])([F:19])[S:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([C@:2]([F:1])([CH3:6])[C:3]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])=[O:4])=[CH:8][CH:9]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 24959564HCID 24959564, compound

Product 1

HCID 24960299HCID 24960299, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3 (0.5 g, 1.6 mmol) in dry CH2Cl2 (10 ml), N,N-carbonyldiimidazole (0.33 g, 2.0 mmol) was added under vigorous stirring. After 1 h methanesulfonamide (0.19 g, 2 mmol) and triethylamine (0.28 mL, 2 mmol) were added and the resulting mixture was left stirring overnight at room temperature. The organic mixture was washed with a saturated solution of NaHCO3 (2×10 mL) and brine (3×10 mL), dried over Na2SO4 and evaporated under vacuum to give pure 17 as a colourless oil (0.60 g, yield 95%). [α]b=+9 (c=1; CH3OH). 1H-NMR (DMSO-d6) δ 7.70 (d, 2H, J=7 Hz), 7.55 (d, 2H, J=7 Hz), 3.05 (s, 3H), 1.85 (d, 3H, J=23 Hz).

Workup

  1. waitthe resulting mixture was left
  2. washThe organic mixture was washed with a saturated solution of NaHCO3 (2×10 mL) and brine (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-9e765c85c754413081ff83b1284ebfba
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

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