Carbon Dioxide → HCID 68838355, compound

HRID 746371Notes

Reaction equation

HRID 746371 reaction equation
C([Li])CCC.[CH3:6][NH:7][S:8]([C:11]1[C:12]([CH3:21])=[CH:13][C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[CH:20]=1)(=[O:10])=[O:9].[C:22](=[O:24])=[O:23].Cl>CCCCCC.O1CCCC1.O.CCOCC>[CH3:6][NH:7][S:8]([C:11]1[C:12]([CH2:21][C:22]([OH:24])=[O:23])=[CH:13][C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[CH:20]=1)(=[O:9])=[O:10]

Participants

9

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 57479790HCID 57479790, compoundHCID 178418339Butyllithium

Product 1

HCID 68838355HCID 68838355, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

100 mL of a 1.5 molare (150 mmol) butyl lithium in hexane were added to a solution of 18 g (75 mmol) 2-methyl-5,6,7,8-tetrahydro-naphthalene-3-sulfonic acid methylamide in 200 mL tetrahydrofuran at −20° C. The resulting mixture was allowed to come to room temperature and was poured onto a mixture of ether and solid CO2. After addition of water the resulting mixture was acidified with dilute HCl and then extracted with CH2Cl2. The CH2Cl2 solution was washed, dried and concentrated. Recrystallization from ether/petroleum ether gave 15.8 g 3-(N-methyl-sulfamoyl)-5,6,7,8-tetrahydro-naphthalene-2-acetic acid (melting point: 153-155° C.).

Workup

  1. customto come to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe CH2Cl2 solution was washed
  4. customdried
  5. concentrationconcentrated
  6. customRecrystallization from ether/petroleum ether

Sources & evidence

ORD record
ord-1de974fa6f2a49998e680cb3eba10301
Source dataset
uspto-grants-2008_07
Patent number
US07393843B2

Reaction notes

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