Methylamine → N-(2-Iodophenyl)-N'-methylurea

Reaction equation

[CH3:1][NH2:2].C1COCC1.[I:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]=[C:16]=[O:17]>>[I:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([NH:2][CH3:1])=[O:17]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 27333851-Iodo-2-isocyanatobenzene

Product 1

HCID 47027879N-(2-Iodophenyl)-N'-methylurea

Procedure

A solution of methylamine in THF (2 M, 19 mL, 39 mmol) was cooled to 0° C. and 2-iodophenylisocyanate (0.68 g, 12.6 mmol) was added dropwise over 5 minutes. The solution was stirred for 30 minutes, after which it was evaporated to dryness in vacuo to yield a white solid (2.05 g) 1H NMR (400 MHz, d6-DMSO): δ 7.81-7.77 (2H, m), 7.53 (1H, s), 7.30-7.26 (1H, m), 6.87 (1H, d, J=4.3 Hz), 6.77-6.73 (1H, m), 2.65 (3H, d, J=4.6 Hz).