Urea → HCID 11627659, compound

HRID 2301572Notes

Reaction equation

HRID 2301572 reaction equation
NC(N)=O.[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([OH:13])[C:7]=1[S:14]([N:17]1[CH2:22][CH2:21][S:20](=[O:23])[CH2:19][CH2:18]1)(=[O:16])=[O:15].[Cl:24][C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[N:32]=[C:33]=[O:34]>>[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][C:33]([NH:32][C:26]2[CH:27]=[CH:28][CH:29]=[C:30]([Cl:31])[C:25]=2[Cl:24])=[O:34])=[C:8]([OH:13])[C:7]=1[S:14]([N:17]1[CH2:18][CH2:19][S:20](=[O:23])[CH2:21][CH2:22]1)(=[O:16])=[O:15]

Participants

4

Reactant 3

HCID 1176UreaHCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 18373537HCID 18373537, compound

Product 1

HCID 11627659HCID 11627659, compoundYield 44%

Procedure

Following the general procedure for urea formation outlined in example 15, 4-chloro-2-hydroxy-3-(1-oxidothiomorpholinosulfonyl)aniline (117 mg, 0.35 mmol) and 2,3-dichlorophenylisocyanate (72 mg, 0.38 mmol) were coupled to form the desired urea (79 mg, 44%). 1H NMR (DMSO-d6): δ 9.34 (s, 1H), 9.27 (s, 1H), 8.28 (d, 1H), 8.05 (m, 1H), 7.32 (m, 2H), 7.21 (d, 1H), 3.75 (m, 2H), 3.65 (m, 2H), 2.89, (m, 4H).

Sources & evidence

ORD record
ord-6c63accb42324e02bb40f0ba33e94659
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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