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

Toluene → N-Pentyl-N-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]carbamoyl Chloride

HRID 425130
Notes
Print preview

Reaction equation

HRID 425130 reaction equation
[CH2:1]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[N:24](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:23]=[N:22][N:21]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].[C:46]([Cl:49])(Cl)=[O:47].[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>O>[CH2:1]([N:6]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[N:24]=[N:23][N:22]([C:56]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:21]=2)=[CH:10][CH:9]=1)[C:46]([Cl:49])=[O:47])[CH2:2][CH2:3][CH2:4][CH3:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 19024425pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amine

Product 1

HCID 59556775N-Pentyl-N-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]carbamoyl Chloride

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
-5 °C

Procedure

Pentyl[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amine (2.9 g, 5.1 mmol) was dissolved in a mixture of toluene (30 mL), water (12 mL) and NaOH (5 equiv). The mixture was cooled to −5° C., and a solution of phosgene in toluene (20% w/w, 3 equiv) was added portionwise. The mixture was stirred vigorously for 0.75 hour at −5° C. The layers were then allowed to separate, the organic layer dried over Na2SO4, and the solvent evaporated to afford the title compound (3.2 g, 5.1 mmol), which was used without further purification.

Workup

  1. customto separate
  2. dry with materialthe organic layer dried over Na2SO4
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-0a07b9dabe0244df9ec2518074307b46
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106082B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes