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

HRID 1795255Notes

Reaction equation

HRID 1795255 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) δ 8.87 (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-bb9f5f1d7f014c2cbf5bcaebf1df7ce9
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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