Stannous Chloride → 4-(3-Methyl-1,2,4-thiadiazol-5-yl)aniline

HRID 2076140Notes

Reaction equation

[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[S:4][N:3]=1.[Sn](Cl)Cl.C(=O)([O-])O.[Na+]>C(O)C>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[S:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 3-methyl-5-(4-nitro-phenyl)-[1,2,4]thiadiazole (104 mg, 0.423 mmol, CAS 800408-77-9) in ethanol (4.3 mL) was added tin(II) chloride (401 mg, 2.1 mmol) and the reaction was heated to 70° C. for 4 hours. The yellow solution was poured onto saturated aqueous sodium hydrogen carbonate solution and the mixture was stirred for 30 minutes. The precipitate was filtered off, washed with water. The solid was heated 3 times with tetrahydrofurane and filtered. The collected organic layers were evaporated to yield crude title compound (110 mg, quant.) as a yellow solid. MS ISP (m/e): 192.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=7.64 (d, 2H), 6.63 (d, 2H), 6.01 (br s, 2H), 2.54 (s, 3H).

Workup

filtrationThe precipitate was filtered off
washwashed with water
temperatureThe solid was heated 3 times with tetrahydrofurane
filtrationfiltered
customThe collected organic layers were evaporated

Sources & evidence

ORD record: ord-4c25030de97041cb9ddca5e67e316ff1
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923450B2

Reaction notes

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