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

HRID 883458Notes

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]

Participants

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

customto separate
dry with materialthe organic layer dried over Na2SO4
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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