Methanesulfonyl chloride → HCID 90019103, compound

HRID 1776976Notes

Reaction equation

HRID 1776976 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[O:14][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 110087787-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 90019103HCID 90019103, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

7-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol (1.0 g, 5.2 mmol) was dissolved in a mixture of DCM (10 mL) and pyridine (10 mL). Then, the reaction mixture was cooled to 0° C. and methane sulphonyl chloride (0.44 mL, 5.7 mmol) was added dropwise, and the reaction mixture was stirred at 60° C. for 2 hours. Next, the reaction mixture was cooled to room temperature and then diluted with ethyl acetate, and washed with 1N HCl, saturated NaHCO3, and brine. The organic solution was dried (Na2SO4) and concentrated to give methanesulfonic acid 7-nitro-1,2,3,4-tetrahydronaphthalen-1-yl ester. Yield 1.34 g (95%). LCMS (ESI): calc. C11H13NO5S=271; obs. low ionization.

Workup

  1. temperatureNext, the reaction mixture was cooled to room temperature
  2. washwashed with 1N HCl, saturated NaHCO3, and brine
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8f85a3a71f3410a97770bf1ca4f6dc8
Source dataset
uspto-grants-2016_02
Patent number
US09266827B2

Reaction notes

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