Urea → N-Butyl-N'-propan-2-ylurea

HRID 1681275Notes

Reaction equation

HRID 1681275 reaction equation
[CH:1]([NH:4][C:5]([NH2:7])=[O:6])([CH3:3])[CH3:2].NC(N)=O.[CH2:12](Br)[CH2:13][CH2:14][CH3:15]>>[CH2:12]([NH:7][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 1176UreaHCID 8002Butyl bromideHCID 12725Isopropylurea

Product 1

HCID 14984935N-Butyl-N'-propan-2-ylureaYield 58%

Procedure

N-butyl-N'-isopropylurea was prepared in a yield of 58% as described in Example 1, but using 2.04 g of N-isopropylurea (20 mmol) as the urea and 2.74 g of butylbromide (20 mmol) as the alkylating agent. 1H-NMR (CDCl3 ; 200 MHz; delta): 5.708 (t; 1H; butyl-NH; JCH2NH =5.5 Hz); 5.490 (d; 1H; isopropyl-NH; JCHNH =7.9 Hz), 3.858 (dq; 1H; isopropyl-CH; JCHNH =7.9 Hz; JCHCH3 =6.5 Hz); 3.135 (dse; 2H; butyl-N--CH2 ; JCH2NH =5.5 Hz; JCH2CH2 =6.7 Hz); 1.498-1.275 (m(tt and tq); 4H; butyl-CH2 --CH2); 1.122 (d; 6H; isopropyl-CH3 ; JCHCH3 = 6.5 Hz); 0.906 (t; 3H; butyl-CH3 ; JCH2CH3 =7.0 Hz) ppm.

Sources & evidence

ORD record
ord-cc5a94edfde34e6291aeef4fc0382f01
Source dataset
uspto-grants-1992_12
Patent number
US05169954

Reaction notes

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