Urea → HCID 11663321, compound

HRID 2301548Notes

Reaction equation

HRID 2301548 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].[Cl:23][C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[N:31]=[C:32]=[O:33]>>[Cl:20][C:19]1[CH:18]=[CH:17][C:16]([NH:21][C:32]([NH:31][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([Cl:30])[C:24]=2[Cl:23])=[O:33])=[C:15]([OH:22])[C:14]=1[S:11]([NH:10][CH2:9][CH2:8][CH2:7][S:6][CH3:5])(=[O:13])=[O:12]

Participants

4

Reactant 3

HCID 1176UreaHCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 18373448HCID 18373448, compound

Product 1

HCID 11663321HCID 11663321, compoundYield 70%

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 2,3dichlorophenylisocyanate (1 82 mg, 0.97 mmol) were coupled to form the desired urea (278 mg, 70%). 1H NMR (MeOD-d4): δ 8.29 (d, 1H), 8.06 (d, 1H), 7.24 (m, 2H), 7.05 (d, 1H), 3.07 (t, 2H), 2.48 (t, 2H), 1.98 (s, 3H) 1.74 (m, 2H).

Sources & evidence

ORD record
ord-4285aee832e54caead4e9e1786a636c2
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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