Water → HCID 15142708, compound

HRID 1886052Notes

Reaction equation

HRID 1886052 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][CH3:14].CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C(Cl)Cl>[CH3:22][S:23]([O:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][CH3:14])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66189732-(2-(Methylamino)-1H-benzo[d]imidazol-1-yl)ethan-1-ol

Product 1

HCID 15142708HCID 15142708, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred mixture of 1-(2-hydroxyethyl)-2-methylamino-1H-benzimidazole (8.05 g, 42.12 mmol), Et3N (4.26 g, 42.12 mmol), and CH2Cl2 (85 mL) was added a solution of MsCl (4.83 g, 42.12 mmol) in CH2Cl2 (10 mL). After 2 hours, H2O was added and the layers were separated. The aqueous phase was extracted with CH2Cl2. The combined extracts were washed with brine, dried, and concentrated to give 8.00 g (71%) of a white solid m.p. 48°-50° C.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. washThe combined extracts were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e65558973f14b0182590fdf9e0088f7
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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