Triethylamine → HCID 86662258, compound

HRID 83903Notes

Reaction equation

HRID 83903 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:11]([N:14]=[CH:15][N:16]([CH3:18])[CH3:17])(=[O:13])=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8][OH:9].CCN(CC)CC.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:9][CH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([S:11](=[O:12])(=[O:13])[N:14]=[CH:15][N:16]([CH3:18])[CH3:17])=[CH:5][C:6]=1[F:10])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66740347N'-(3,5-difluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide

Product 1

HCID 86662258HCID 86662258, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N′-(3,5-difluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethyl-formimidamide (80 g, 287 mmol) in DCM (500 mL) was added Et3N (121 mL, 862 mmol, 3 eq) and methanesulfonylchloride (27 mL, 245 mmol, 1.2 eq) successively at 0° C. After 30 min, the reaction mixture was extracted with DCM (300 mL×3). The combined extracts were washed with water (1 L), dried over MgSO4, concentrated and then purified by chromatography (silica, DCM/EtOAc, 1:1) to give 4-(N-((dimethylamino)methylene)sulfamoyl)-2,6-difluorobenzyl methanesulfonate (77.5 g, 28% over 4 steps) as a ivory solid. 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.59-7.39 (m, 2H), 5.32 (s, 2H), 3.18 (s, 3H), 3.09 (s, 3H), 3.08 (s, 3H).

Workup

  1. extractionthe reaction mixture was extracted with DCM (300 mL×3)
  2. washThe combined extracts were washed with water (1 L)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by chromatography (silica, DCM/EtOAc, 1:1)

Sources & evidence

ORD record
ord-9ddffb02a04e4ad4974107d345e2b348
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…