Triethylamine → HCID 19864849, compound

HRID 1200253Notes

Reaction equation

HRID 1200253 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][O:12][C:13]1[CH:14]=[C:15](N)[CH:16]=[CH:17][CH:18]=1.[CH2:20]([N:22](CC)CC)[CH3:21].C([S:29](Cl)(=[O:31])=[O:30])C>O1CCCC1>[CH2:20]([NH:22][S:29]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH2:11][C:3]2[N:2]([CH3:1])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N:4]=2)[CH:14]=1)(=[O:31])=[O:30])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 14548113HCID 14548113, compound

Product 1

HCID 19864849HCID 19864849, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[(1-methyl-2-benzimidazolyl)methoxy]benzenamine (2 g) and triethylamine (0.79 g) in tetrahydrofuran (100 ml) at room temperature is slowly added a solution of ethanesulfonyl chloride (1.0 g) in tetrahydrofuran. The reaction is stirred for 1 hour. The mixture is filtered through a pad of Celite and silica gel and the solvent is removed in vacuo giving an oil. The oil is purified by HPLC and crystallized from hexane to give 1.0 g (37% yield) of product, m.p. 169°-173° C.

Workup

  1. filtrationThe mixture is filtered through a pad of Celite and silica gel
  2. customthe solvent is removed in vacuo
  3. customgiving an oil
  4. customThe oil is purified by HPLC
  5. customcrystallized from hexane

Sources & evidence

ORD record
ord-afaa4bbc6aab464bbf563e4c6568e28c
Source dataset
uspto-grants-1990_02
Patent number
US04904786

Reaction notes

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