Dimethylamine → 3-(5,5-Dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-urea

HRID 595080

Reaction equation

[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][C:8]([CH3:13])([CH3:12])[CH2:7][C:5]=2[N:6]=1.C1N=[CH:17][N:16]([C:19](N2C=NC=C2)=[O:20])[CH:15]=1.C1CCN2C(=NCCC2)CC1.CNC>C(#N)C>[CH3:12][C:8]1([CH3:13])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:19](=[O:20])[N:16]([CH3:17])[CH3:15])[S:3][C:4]=2[C:10](=[O:11])[CH2:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one (151 g, 0.768 mol) in acetonitrile (5 L) are added CDI (249 g, 1.53 mol) and DBU (233 g, 1.53 mol). The reaction mixture is stirred overnight at 100° C. Dimethylamine (310 g, 3.83 mol) is added at RT and the stirring is continued overnight at 100° C. After cooling to RT, the reaction mixture is concentrated in vacuo and the residue is poured into ice water. The pH of the mixture is adjusted to pH 5 with HCl (6 M). The aqueous mixture is extracted with ethyl acetate (4×500 mL). The combined organic layers are washed with brine (500 mL) and dried over anhydrous Na2SO4. The solvent is evaporated in vacuo to give crude product. The crude product is washed with water to give 3-(5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-urea (169 g, 82% yield).

Workup

waitthe stirring is continued overnight at 100° C
temperatureAfter cooling to RT
concentrationthe reaction mixture is concentrated in vacuo
additionthe residue is poured into ice water
extractionThe aqueous mixture is extracted with ethyl acetate (4×500 mL)
washThe combined organic layers are washed with brine (500 mL)
dry with materialdried over anhydrous Na2SO4
customThe solvent is evaporated in vacuo
customto give crude product
washThe crude product is washed with water

Sources & evidence

ORD record: ord-6999cae8d4f342d0ae16606ad2a34978
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243000B2

Linked notes

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