Urea → HCID 11643132, compound

HRID 2301598Notes

Reaction equation

HRID 2301598 reaction equation
NC(N)=O.[C:5]([O:9][C:10]([NH:12][CH:13]([C:31]([OH:33])=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]([NH2:29])[C:23]=1[OH:30])(=[O:21])=[O:20])=[O:11])([CH3:8])([CH3:7])[CH3:6].[Cl:34][C:35]1[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=1[N:42]=[C:43]=[O:44]>>[C:5]([O:9][C:10]([NH:12][CH:13]([C:31]([OH:33])=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]1[C:23]([OH:30])=[C:24]([NH:29][C:43]([NH:42][C:36]2[CH:37]=[CH:38][CH:39]=[C:40]([Cl:41])[C:35]=2[Cl:34])=[O:44])[CH:25]=[CH:26][C:27]=1[Cl:28])(=[O:20])=[O:21])=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 3

HCID 1176UreaHCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 18373463HCID 18373463, compound

Product 1

HCID 11643132HCID 11643132, compoundYield 30.2%

Procedure

Following the general procedure for urea formation outlined in example 15, N-[5-(tert-butoxycarbonylamino)-5-carboxypentyl]-3-amino-6-chloro-2-hydroxybenzenesulfonamide (233 mg, 0.518 mmol) and 2,3-dichlorophenylisocyanate (98 mg, 0.518 mmol) were coupled to form the desired urea (100 mg, 30%). LC-MS (m/z) 641.2 (M+).

Sources & evidence

ORD record
ord-7a34cc691ed94cff820cf9833c2bb7b0
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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