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

HRID 9121
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887MethanolSolvent
HCID 8900
Heptane
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes