Diethylcarbamoyl chloride → HCID 66771878, compound

HRID 1645316Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:26]([N:28]([CH2:32][CH3:33])[C:29](Cl)=[O:30])[CH3:27]>CN(C1C=CN=CC=1)C.O.C(O)(=O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][C:29](=[O:30])[N:28]([CH2:32][CH3:33])[CH2:26][CH3:27])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 66 °C

Procedure

Charge a vessel with 2-(4-methoxy-phenyl)-benzo[b]thiophen-6-ol (1.000 mol, 256.3 g), 99% DMAP (0.100 mol, 12.34 g), and THF (10.0 L/kg, 2.56 L). Add 99% triethylamine (1.050 mol, 107.3 g) and 97% diethylcarbamyl chloride (DEC-Cl) (1.050 mol, 146.8 g). Heat the contents of the reactor to reflux/66° C. Stir 4 hours or until reaction is complete as determined by HPLC. Begin to cool to 50° C. and add acetic acid solution made up of DI water (3.0 L/kg, 769 mL) and glacial acetic acid (0.300 mol, 18.02 g). Separate the layers at 50° C., and remove the bottom aqueous layer. Cool the organic layer to −5 to 0° C. (−20° C. to ambient is acceptable). The organic layer contains a solution of diethyl-carbamic acid 2-(4-methoxy-phenyl)-benzo[b]thiophen-6-yl ester which is most conveniently carried directly to the next step, the bromination step.

Workup

temperatureHeat the contents of the reactor
temperatureto cool to 50° C.
customSeparate the layers at 50° C.
customremove the bottom aqueous layer
temperatureCool the organic layer to −5 to 0° C. (−20° C. to ambient is acceptable)

Sources & evidence

ORD record: ord-f846c71f5d194df996f11fec6349bd14
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124776B2

Reaction notes

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