Urea → HCID 68468856, compound

HRID 1891376Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH2:22].[NH2:23][C:24](N)=[O:25].CCOCC>ClCCCl.CC(O)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:9])=[O:10])=[CH:4][C:3]=1[NH:22][C:24]([NH2:23])=[O:25]

Participants

Conditions

Temperature: 100 °C

Procedure

To 2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine (3.4 g, 10 mmol) in DCE (20 mL) and HOAc (20 mL) was added urea (1.2 g, 20 mmol). The mixture was stirred at 100° C. for 24 hrs and was then partitioned between DCM (150 mL) and sat. NaHCO3 solution (150 mL). Additional solid NaHCO3 was added until the aqueous layer pH value was 8. The organic layer was separated, washed with saturated NaHCO3 and brine, dried over MgSO4 and evaporated to obtain a yellow oil. The oil was re-dissolved in DCM (10 mL) and ether (50 mL) and stood at rt for 12 hrs to give [2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-urea (1.7 g) as a white solid. MS: 379.7 (M+H)+; tR=6.67 min (method 2).

Workup

customwas then partitioned between DCM (150 mL) and sat. NaHCO3 solution (150 mL)
additionAdditional solid NaHCO3 was added until the aqueous layer pH value
customThe organic layer was separated
washwashed with saturated NaHCO3 and brine
dry with materialdried over MgSO4
customevaporated
customto obtain a yellow oil

Sources & evidence

ORD record: ord-3e1827b1cf4d435e84ce6a9ae50cf33e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507536B2

Reaction notes

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