Ammonia → [4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-urea

HRID 1713631Notes

Reaction equation

HRID 1713631 reaction equation
[N:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)=[C:2]=S.[NH3:18].C[OH:20]>>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:4]([NH:1][C:2]([NH2:18])=[O:20])=[CH:5][CH:6]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887Methanol2×HCID 118461221-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidine

Product 1

HCID 68704441[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-urea

Procedure

A mixture of 1-[2-(4-isothiocyanato-phenoxy)-ethyl]-pyrrolidine (0.355 g, 1.43 mmol), MeOH (2.75 mL) and a 2M solution of NH3 in MeOH (2.75 mL, 5.49 mmol, 3.84 equiv) is heated in a sealed tube at 60° C. for 1 h, under an argon atmosphere. The reaction mixture is allowed to cool to RT and concentrated in vacuo to afford the title compound as a dark brown solid: ES-MS: 266.0 [M+H]+; single peak at tR=3.99 min (System 1).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ecf8666e73c48d9b1328f290a850835
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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