Triethylamine → HCID 15142712, compound

HRID 1886055Notes

Reaction equation

HRID 1886055 reaction equation
O[CH2:2][CH2:3][N:4]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5]1.C[CH2:17][N:18](CC)CC.CS(Cl)(=O)=O.CN.CCO>C(Cl)Cl>[CH3:17][NH:18][CH2:2][CH2:3][N:4]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19876800HCID 19876800, compoundHCID 22028356Methylamine ethanol

Product 1

HCID 15142712HCID 15142712, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred suspension of 1-N-(2-hydroxyethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (882 mg, 4.34 mmol) in CH2Cl2 (18 mL) was added Et3N (0.67 mL, 4.77 mmol) and MsCl (0.37 mL, 4.77 mmol). The resulting solution was stirred at room temperature for 1 hour, washed with brine, dried (MgSO4) and concentrated to give an off-white solid. 33% CH3NH2 /EtOH (45 mL) was added and the solution was stirred at room temperature over the weekend. The mixture was concentrated, taken up in 10% aqueous HOAc (20 mL) and extracted with EtOAc. The extracts were dried (MgSO4) and concentrated to give 738 mg (79%) of an off-white solid m.p. 60°-63° C.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 1 hour
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give an off-white solid
  6. stirringthe solution was stirred at room temperature over the weekend
  7. concentrationThe mixture was concentrated
  8. extractionextracted with EtOAc
  9. dry with materialThe extracts were dried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-35925ca27ad34e4cbaa7e41ae522a851
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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