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Water → 5-(4-Bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one

HRID 1024606
Notes
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Reaction equation

HRID 1024606 reaction equation
C(O[C:4]([C:6]1[N:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)[C:10]=1[NH2:11])=[O:5])C.[Br:22][C:23]1[CH:38]=[CH:37][C:26]([C:27](Cl)=[N:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.O>ClC(Cl)C.C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]2[N:28]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:4](=[O:5])[C:6]3[N:7]=[N:8][N:9]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:19])=[O:20])[CH:13]=4)[C:10]=3[N:11]=2)=[CH:37][CH:38]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 962WaterHCID 578981714-bromo-N-(4-chloro-phenyl)-benzimidoyl chlorideHCID 578993755-amino-1-(3-methanesulfonyl-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Product 1

HCID 578994115-(4-Bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one

Reagents, catalysts & solvents 3

HCID 24193
Titanium Tetrachloride
Catalyst
HCID 6344DichloromethaneSolvent
HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-amino-1-(3-methanesulfonyl-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (310 mg, 1 mmol), 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride (1.2 mmol) and TiCl4 (2 mmol) in anhydrous dichloroethane (5 mL) is heated to 150° C. for 14 h. After cooling down to room temperature, the mixture is diluted with CH2Cl2 (20 mL) and treated with water (30 mL). The solid is collected by filtration and washed with MeOH (5 ml) to provide the crude 5-(4-bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one as yellow solid which is used for next step without further purification.

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationThe solid is collected by filtration
  3. washwashed with MeOH (5 ml)

Sources & evidence

ORD record
ord-5bf6fc0e559442b3bc8000ea74818e68
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722691B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes