Sodium Hydroxide → HCID 9936477, compound

HRID 884512Notes

Reaction equation

[O-:1][C:2]#[N:3].[Na+].[NH2:5][CH2:6][CH2:7][N:8]1[C:25](=[N:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:30]=[CH:29][C:28]=2[CH:36]([CH3:38])[CH3:37])[CH:24]=[C:11]2[C:12]3[C:17]([CH2:18][CH2:19][N:10]2[C:9]1=[O:39])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3.[OH-].[Na+]>O.Cl>[C:2]([NH:5][CH2:6][CH2:7][N:8]1[C:25](=[N:26][C:27]2[C:28]([CH:36]([CH3:37])[CH3:38])=[CH:29][CH:30]=[CH:31][C:32]=2[CH:33]([CH3:35])[CH3:34])[CH:24]=[C:11]2[C:12]3[C:17]([CH2:18][CH2:19][N:10]2[C:9]1=[O:39])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)(=[O:1])[NH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium cyanate (0.87 g, 13.4 mmol) in water (20 ml) was added dropwise to a stirred solution of amine 3 (3.2 g, 6.7 mmol) in water (100 ml) and 1M HCl (13.4 ml) at 80° C. After stirring for 4 h at 80° C. the mixture was cooled and basified with 2M NaOH. The mixture was extracted with CH2Cl2 until no more product remained in the organic phase. The organic phases were combined, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography [dichloromethane/methanol (97:3)] and the isolated product taken up in a mixture of dichloromethane and ether which on concentration afforded the title compound (0.6 g, 17%) as a pale yellow foam.

Workup

temperaturewas cooled
extractionThe mixture was extracted with CH2Cl2 until no more product
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography [dichloromethane/methanol (97:3)]
additionthe isolated product taken up in a mixture of dichloromethane and ether which on concentration

Sources & evidence

ORD record: ord-022b987727674df6a68fd112478c13dd
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242127B2

Reaction notes

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