Acetic Acid → HCID 66771878, compound

HRID 1645314Notes

Reaction equation

HRID 1645314 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].C(O)(=O)C>CN(C1C=CN=CC=1)C.O.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

8

Reactant 4

HCID 176Acetic AcidHCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 98379882-(4-Methoxyphenyl)-1-benzothiophene-6-ol

Product 1

HCID 66771878HCID 66771878, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine 2-(4-methoxy-phenyl)-benzo[b]thiophen-6-ol (10.00 g, 39.01 mmoles), DMAP (478 mg, 3.87 mmoles), and THF (100 mL) under nitrogen and then add triethylamine (4.19 g, 41.03 mmoles) and diethylcarbamoyl chloride (5.73 g, 40.99 mmoles). Heat the mixture to reflux and maintain for 6 hours. Cool the reaction to 50° C. Add a mixture of water (20 mL) and acetic acid (0. 67 mL, 11.68 mmoles). Separate the phases and discard the aqueous phase. This yields a solution of diethyl-carbamic acid 2-(4-methoxy-phenyl)-benzo[b]thiophen-6-yl ester in THF.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. temperaturemaintain for 6 hours
  4. temperatureCool
  5. customthe reaction to 50° C
  6. additionAdd
  7. customSeparate the phases

Sources & evidence

ORD record
ord-0e6cafdcc62e4f5190ea81f47009b2e0
Source dataset
uspto-grants-2012_02
Patent number
US08124776B2

Reaction notes

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