Thionyl Chloride → 5-(1H-benzo[d][1,2,3]triazol-1-yl)-4-(naphthalen-1-yl)-1,2,3-thiadiazole

HRID 386396Notes

Reaction equation

HRID 386396 reaction equation
[N:1]1([CH2:10]/[C:11](=[N:22]\[NH:23][S:24](C2C=CC(C)=CC=2)(=O)=O)/[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.O=S(Cl)Cl>>[N:1]1([C:10]2[S:24][N:23]=[N:22][C:11]=2[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 87167245N-[(Z)-[2-(benzotriazol-1-yl)-1-naphthalen-1-ylethylidene]amino]-4-methylbenzenesulfonamide

Product 1

HCID 668209545-(1H-benzo[d][1,2,3]triazol-1-yl)-4-(naphthalen-1-yl)-1,2,3-thiadiazole

Conditions

Temperature
60 °C

Procedure

A mixture of (Z)—N′-(2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(naphthalen-1-yl)ethylidene)-4-methylbenzenesulfonohydrazide (1 g, 2.19 mmol) and SOCl2 (25 mL) was stirred at 60° C. for 18 h and then concentrated and purified by TLC (100% DCM) to afford 5-(1H-benzo[d][1,2,3]triazol-1-yl)-4-(naphthalen-1-yl)-1,2,3-thiadiazole as an amber solid.

Workup

  1. concentrationconcentrated
  2. custompurified by TLC (100% DCM)

Sources & evidence

ORD record
ord-930b32bd524648e1850db6ebee9c4e5e
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

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