HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Phosgene → HCID 11486440, compound

HRID 2266950
Notes
Print preview

Reaction equation

HRID 2266950 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]1([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:5]1([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:1]([N:28]2[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][O:22][CH2:21][CH2:20][OH:19])[CH2:26][CH2:27]2)=[O:2])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 1394361-[2-(2-Hydroxyethoxy)ethyl]piperazineHCID 3653932-(Phenylthio)aniline

Product 1

HCID 11486440HCID 11486440, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8471Triethylamine
Solvent
2×

Conditions

Temperature
-50 °C

Procedure

The reaction was carried out without isolation of intermediates in a one pot synthesis. Toluene (30 ml) and phosgene solution (20% in xylene, 9.1 ml, 17.16 mmol) were charged into a reaction flask. The mixture was cooled to −50° C. A mixture of 2-phenylsulfanylphenylamine (3 g, 14.9 mmol), triethylamine (2.4 ml, 17.1 mmol) and toluene (5 ml) was charged into the reaction flask at −50° C. during 5 min. The mixture was allowed to reach room temperature and it was stirred at room temperature for 1.5 h. Then the reaction mixture was added to another reaction flask at −10-0° C., containing the cooled mixture of 1-[2-(hydroxyethoxy)-ethyl]-piperazine, triethylamine (2.7 ml) and toluene (20 ml). The reaction mixture was stirred at room temperature for 1.5 h. Precipitated triethylamine hydrochloride was filtered off. The resulting toluene solution was washed twice with saturated NaCl-water (10 ml), dried with K2CO3 and evaporated in vacuo. The yield of 4-[2-(2-hydroxyethoxy)-ethyl]-piperazine-carboxylic acid (2-phenylsulfanyl-phenyl)-amide was 4.76 g.

Workup

  1. customThe reaction was carried out without isolation of intermediates in a one pot synthesis
  2. additionwas charged into the reaction flask at −50° C. during 5 min
  3. customto reach room temperature
  4. additionThen the reaction mixture was added to another reaction flask at −10-0° C.
  5. additioncontaining
  6. stirringThe reaction mixture was stirred at room temperature for 1.5 h
  7. filtrationPrecipitated triethylamine hydrochloride was filtered off
  8. washThe resulting toluene solution was washed twice with saturated NaCl-water (10 ml)
  9. dry with materialdried with K2CO3
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-cd3e37919d144f559d2c8b9edcb5f2c5
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858777B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes