Potassium Hydroxide → 1-(7-Acetylenyl-2-benzothiazolyl)-3-ethylurea

HRID 9121

Reaction equation

HRID 9121 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:15]2[S:14][C:13]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(C)C.[OH-].[K+].CN(C=O)C.CO>CCCCCCC.CO>[C:6]([C:7]1[C:15]2[S:14][C:13]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)#[CH:5]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 21901440N,N-dimethylformamide methanolHCID 219855381-(7-Trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219856501-(7-Acetylenyl-2-benzothiazolyl)-3-ethylureaYield 15.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 1-(7-trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea 2 (0.050 g, 0.16 mmol) and 1M aqueous KOH solution (0.16 mL, 0.16 mmol, 1.0 eq) in 1.5 mL of 2/1 mixture of DMF/MeOH was stirred at room temperature for about 2 hours. The mixture was taken up in 10 mL MeOH and the precipitation was filtered off. The mother liquid was concentrated and purified by prep HPLC to give the desired compound 0.006 g (15%). LC/MS 246 (M+1); LC retention time 2.77 min.

Workup

  1. customthe precipitation
  2. filtrationwas filtered off
  3. concentrationThe mother liquid was concentrated
  4. custompurified by prep HPLC

Sources & evidence

ORD record
ord-8abe128357e5495cb8583bed1bcfdda2
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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