Triethylamine → HCID 11949830, compound

HRID 221955Notes

Reaction equation

HRID 221955 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[C:8]2=[O:23])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C([O-])(O)=O.[Na+]>O.C1COCC1>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:9]2[CH2:10][CH2:11][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:34]([CH3:33])(=[O:36])=[O:35])=[CH:25][CH:24]=3)[C:8]2=[O:23])=[CH:14][CH:15]=1)([CH3:20])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59707065HCID 59707065, compound

Product 1

HCID 11949830HCID 11949830, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-imidazolidin-2-one (F) (410 mg, 1.22 mmol) and triethylamine (0.2 mL, 1.44 mmol) in abs. THF there was added a solution of methanesulphonyl chloride (0.12 mL, 1.56 mmol) in 0.8 mL of abs. THF within a period of 20 min. The reaction mixture was stirred over a period of 15 h at RT, sat. NaHCO3 solution (10 mL) was added, and the mixture was stirred for 30 min. H2O (30 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined organic phases were washed with sat. NaCl solution, dried over Na2SO4, and the solvent was removed in vacuo. Following purification, by column chromatography, of the residue (SiO2, EtOAc/cyclohexane 2:1), there were obtained the desired product N-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}methanesulfonamide (4) (70 mg, 14% of theory, mp: 166-168° C.) and N-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}-N,N-bis(methanesulfonyl)imide (G) (160 mg, mp: 184-187° C.).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionthe mixture was extracted with EtOAc (3×20 mL)
  3. washThe combined organic phases were washed with sat. NaCl solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. custompurification

Sources & evidence

ORD record
ord-29f0bcd04c1e4c6d81f9b06873afb484
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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