Dicyclohexylamine → 1,1-Dicyclohexyl-3-(5-thiocyanato-thiazol-2-yl)-urea

HRID 731410Notes

Reaction equation

[S:1]([C:4]1[S:8][C:7]([NH2:9])=[N:6][CH:5]=1)[C:2]#[N:3].[CH:10]1([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C1C[O:26][CH2:25]C1>CN(C1C=CN=CC=1)C>[CH:17]1([N:16]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:25]([NH:9][C:7]2[S:8][C:4]([S:1][C:2]#[N:3])=[CH:5][N:6]=2)=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

Conditions

Temperature: 65 °C

Procedure

An equimolar mixture of 1,1-carbonyldiimidazole, 5-thiocyanato-thiazol-2-ylamine (commercial available or prepared as described in J. Am. Chem. Soc 71, 4007, 1949 or J. Med. Chem., 20, 572, 1977) and DMAP (5 mol %) in THF was heated for 2 h at 60-70° C. and then cooled to room temperature. Dicyclohexyl amine (1 equivalent) was added and the reaction is stirred overnight at room temperature. The reaction mixture was quenched with water. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude product was purified by flash chromatography (heptane:EtOAc 100:0 50:50) affording 1,1-dicyclohexyl-3-(5-thiocyanato-thiazol-2-yl)-urea as an oil.

Workup

temperaturecooled to room temperature
customThe reaction mixture was quenched with water
customThe organic phase was isolated
extractionthe aqueous phase was extracted with CH2Cl2
customthe combined organic phases were dried
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography (heptane:EtOAc 100:0 50:50)

Sources & evidence

ORD record: ord-42cb558c105346f193a7dcce173b58d2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582769B2

Reaction notes

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