Triethylamine → HCID 20195954, compound

HRID 653178Notes

Reaction equation

HRID 653178 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)N.[CH2:19]([N:21](CC)CC)[CH3:20].C([S:28](Cl)(=[O:30])=[O:29])C>O1CCCC1>[CH2:19]([NH:21][S:28]([C:14]1[CH:16]=[CH:17][CH:18]=[C:12]([O:11][CH2:10][C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH:13]=1)(=[O:30])=[O:29])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 13631156HCID 13631156, compound

Product 1

HCID 20195954HCID 20195954, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[(2-benzothiazolyl)methoxy]aniline (2.0 g) and triethylamine (0.79 g) in tetrahydrofuran (50 ml) at room temperature is slowly added a solution of ethane sulfonyl 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 1.4 g (51% yield) of product, m.p. 111°-113° 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-6e24f8d46cde49729fef7057caba01a6
Source dataset
uspto-grants-1987_06
Patent number
US04675405

Reaction notes

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