Methanesulfonyl chloride → HCID 21184517, compound

HRID 1385282Notes

Reaction equation

HRID 1385282 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:17][C:6]2=[C:7]([C:12]3[CH:16]=[CH:15][NH:14][N:13]=3)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:18])[CH2:3]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.C1COCC1.CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:19])[CH2:17][C:6]2=[C:7]([C:12]3[CH:16]=[CH:15][N:14]([S:21]([CH3:20])(=[O:23])=[O:22])[N:13]=3)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:18])[CH2:3]1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178503625HCID 178503625, compound

Product 1

HCID 21184517HCID 21184517, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of 6,6-dimethyl-3-methylthio-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (70 mg, 0.24 mmol) in CH2Cl2:THF (5:1, 6 mL), was added methanesulphonyl chloride (36 μL, 0.48 mmol) and 4-dimethylaminopyridine (58 mg, 0.48 mmol). The mixture was stirred at room temperature overnight then diluted with CH2Cl2 (10 mL) and washed with water (2×10 mL). The organic layer was separated, dried (Na2SO1) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2:MeOH (95:5), to give the title compound (38 mg, 43%) as a pale yellow solid. mp 193-195° C. Found: C, 47.72; H, 4,71; N, 7.16%. C15H18N2S3O3.0.3 (H2O) requires: C, 47.93, H, 4.99; N, 7.45%. 1HNMR (360 Hz, d6-DMSO) δ 1.02 (6H, s), 2.41 (2H, s), 2.64 (3H, s), 2.90 (2H, s), 3.61 (3H, s), 6.91 (1H, d, J=2.8 Hz). MS (ES+) 371 (M+1).

Workup

  1. washwashed with water (2×10 mL)
  2. customThe organic layer was separated
  3. customdried (Na2SO1)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with CH2Cl2:MeOH (95:5)

Sources & evidence

ORD record
ord-a05252458fee4a25a03edc5037693080
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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