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

HRID 857697Notes

Reaction equation

HRID 857697 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-6721374fc8d942ddbe88fcd47613fcdb
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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