Urea → HCID 11670678, compound

HRID 2301550Notes

Reaction equation

HRID 2301550 reaction equation
NC(N)=O.[CH3:5][S:6][CH2:7][CH2:8][CH2:9][NH:10][S:11]([C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([NH2:21])[C:15]=1[OH:22])(=[O:13])=[O:12].[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]=[C:31]=[O:32]>>[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31]([NH:21][C:16]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([S:11]([NH:10][CH2:9][CH2:8][CH2:7][S:6][CH3:5])(=[O:13])=[O:12])[C:15]=1[OH:22])=[O:32]

Participants

4

Reactant 3

HCID 1176UreaHCID 1370972-Bromophenyl isocyanateHCID 18373448HCID 18373448, compound

Product 1

HCID 11670678HCID 11670678, compoundYield 74%

Procedure

Following the general procedure for urea formation outlined in example 15, N-(3-methylthiopropyl)-3-amino-6-chloro-2-hydroxybenzenesulfonamide (250 mg, 0.80 mmol) and 2-bromophenylisocyanate (191 mg, 0.97 mmol) were coupled to form the desired urea (300 mg, 74%). 1H NMR (MeOD-d4): δ 8.28 (d, 1H), 7.91 (d, 1H), 7.58 (d, 1H), 7.32 (t, 1H), 7.05 (d, 1H), 7.00 (t, 1H), 3.08 (t, 2H), 2.48 (t, 2H), 1.98 (s, 3H), 1.74 (m, 2H).

Sources & evidence

ORD record
ord-bd98b8f5e1e247c99b0777528f25fbf5
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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