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

HRID 883458
Notes
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Reaction equation

HRID 883458 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-554e47dc9857434e8ca0eb1997ef86ac
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236839B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes