Hydrochloric Acid → 1-(6-Acetylenyl-2-benzothiazolyl)-3-ethylurea

HRID 9131

Reaction equation

HRID 9131 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:21]=[CH:20][C:10]2[N:11]=[C:12]([NH:14][C:15]([NH:17][CH2:18][CH3:19])=[O:16])[S:13][C:9]=2[CH:8]=1)(C)C.[OH-].[K+].Cl>CO.CCOC(C)=O>[C:6]([C:7]1[CH:21]=[CH:20][C:10]2[N:11]=[C:12]([NH:14][C:15]([NH:17][CH2:18][CH3:19])=[O:16])[S:13][C:9]=2[CH:8]=1)#[CH:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 219855421-(6-Trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855921-(6-Acetylenyl-2-benzothiazolyl)-3-ethylureaYield 5.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(6-trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea (0.0710 g, 0.22 mmol) and 1M aqueous KOH solution (1.22 mL, 1.22 mmol, 5.5 eq) in 1.5 mL MeOH was stirred at room temperature for about 2 hours. The mixture acidified with 1 M HCl, then taken up in 20 mL AcOEt, and the aqueous phase was extracted with 10 mL AcOEt. The combined organic portions were dried (MgSO4), concentrated, and purified by HPLC to give the desired compound 0.003 g (5%). LC/MS 246 (M+1); LC retention time 2.84 min.

Workup

  1. extractionthe aqueous phase was extracted with 10 mL AcOEt
  2. dry with materialThe combined organic portions were dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-e28f5a27454f477e9bdcf8a67a519fdf
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

Loading…