Methanesulfonyl chloride → HCID 18789983, compound

HRID 1106890Notes

Reaction equation

HRID 1106890 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:10]=1[O:11][CH2:12][CH2:13]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH2:32][CH2:33][N:34](CC)[CH3:35]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:10]=1[O:11][CH2:12][CH2:13][N:34]([CH2:33][CH2:32][C:31]1[CH:38]=[CH:39][C:40]([O:41][CH3:42])=[C:29]([O:28][CH3:27])[CH:30]=1)[CH3:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 18789952HCID 18789952, compoundHCID 18789965HCID 18789965, compound

Product 1

HCID 18789983HCID 18789983, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Benzyloxy-4-nitrophenoxy)ethanol (400 mg, 1.383 mmol) was dissolved in pyridine (5 ml); after cooling at 0° C., methanesulfonyl chloride (0.22 ml, 2.76 mmol) was slowly added dropwise, followed by stirring at room temperature for 2 h. The solvent was evaporated under vacuum and the residue was diluted with a saturated aqueous solution of sodium bicarbonate (10 ml), followed by extraction with chloroform (100 ml). The extracted organic layer was dried with sodium sulfate and the solvent was evaporated; the resulting residue was dissolved in 15 ml of a 1:2 solvent system of ethanol and acetonitrile and, thereafter, 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (0.765 ml, 4.148 mmol) was added, followed by stirring at the reflux temperature for 8 h. The reaction solution was cooled to room temperature and thereafter the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 1:1 solvent system of n-hexane and ethyl acetate as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound 1-(2-benzyloxy-4-nitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (600 mg).

Workup

  1. customThe solvent was evaporated under vacuum
  2. additionthe residue was diluted with a saturated aqueous solution of sodium bicarbonate (10 ml)
  3. extractionfollowed by extraction with chloroform (100 ml)
  4. dry with materialThe extracted organic layer was dried with sodium sulfate
  5. customthe solvent was evaporated
  6. dissolutionthe resulting residue was dissolved in 15 ml of a 1:2 solvent system of ethanol and acetonitrile
  7. stirringby stirring at the reflux temperature for 8 h
  8. temperatureThe reaction solution was cooled to room temperature
  9. customthe solvent was evaporated
  10. customthe resulting residue was purified
  11. additionThe fractions containing the product
  12. customwere collected
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6f1fa1a9a7b240479065a1bfbd2d0213
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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