Water → 2-[1,2,3]Thiadiazol-4-yl-benzylamine

HRID 397498Notes

Reaction equation

HRID 397498 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[N:13][S:14][CH:15]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[S:14]1[CH:15]=[C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][NH2:1])[N:12]=[N:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 218662814-(2-Azidomethyl-phenyl)-[1,2,3]thiadiazole

Product 1

HCID 114012722-[1,2,3]Thiadiazol-4-yl-benzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(2-azidomethyl-phenyl)-[1,2,3]thiadiazole (1.0 g, 4.6 mmol), triphenylphosphine (1.4 g, 5.5 mmol) and water (0.12 ml, 6.9 mmol) in tetrahydrofuran (20 ml) was stirred at room temperature overnight. Solvent evaporation and flash chromatography (silica gel, chloroform-2-propanol, 95:5-92:8) gave 2-[1,2,3]thiadiazole-4-yl-benzylamine; 1H NMR (CDCl3, 300 MHz) δ8.87 (s, 1H), 7.67 (d, 1H, J=8 Hz), 7.45 (m, 3H), 3.88 (s, 2H).

Workup

  1. customSolvent evaporation and flash chromatography (silica gel, chloroform-2-propanol, 95:5-92:8)

Sources & evidence

ORD record
ord-6f2b996dda2942d4b2c01d1a5c9c0b6f
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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