2-Chloroaniline → N-(2-chlorophenyl)-2-(1-naphthalen-1-yltetrazol-5-yl)sulfanylacetamide

HRID 1988797Notes

Reaction equation

[C:1]1([N:11]2[C:15]([S:16][CH2:17][C:18]([OH:20])=O)=[N:14][N:13]=[N:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH:24][C:18](=[O:20])[CH2:17][S:16][C:15]1[N:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[N:12]=[N:13][N:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-{{1-(1-Naphthalenyl)-1H-tetrazol-5-yl}thio}acetic acid (500 mg, 1.75 mmol) and 2-chloroaniline (202 μL, 1.92 mmol) were dissolved in dry pyridine (8 mL). This solution was cooled to 0° C. and POCl3 (0.179 mL) was added dropwise. The mixture was stirred at 0° C. for 1 h, quenched with a few drops of water, and concentrated under reduced pressure. The crude product was dissolved in CH2Cl2 (100 mL) and the resulting solution was successively washed with water (2×30 ml) and brine (30 ml), dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (CH2Cl2:(CH3)2CO, 95:5) to afford the title compound (643 mg, 85% yield) as a solid.

Workup

customquenched with a few drops of water
concentrationconcentrated under reduced pressure
dissolutionThe crude product was dissolved in CH2Cl2 (100 mL)
washthe resulting solution was successively washed with water (2×30 ml) and brine (30 ml)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash column chromatography (CH2Cl2:(CH3)2CO, 95:5)

Sources & evidence

ORD record: ord-6e5e15df3081449e93c1907241536eb1
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642277B2

Reaction notes

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