Potassium Carbonate → HCID 70543145, compound

HRID 1156174Notes

Reaction equation

HRID 1156174 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3[CH:10]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:12]=[CH:13][C:7]=3[C:6]=2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:26][N:27]([CH2:29][CH2:30]Cl)[CH3:28]>CN(C)C=O>[ClH:1].[CH3:26][N:27]([CH3:28])[CH2:29][CH2:30][O:16][C:15](=[O:17])[CH2:14][C:11]1[CH:12]=[CH:13][C:7]2[C:6]3[CH:18]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[S:9][C:8]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 130651048-Chlorodibenzothiophene-3-acetic acid

Product 1

HCID 70543145HCID 70543145, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.76 g. of 8-chlorodibenzothiophene-3-acetic acid, 3.04 g. of potassium carbonate, 1.73 g. of dimethylaminoethyl chloride hydrochloride, and 250 ml. of dimethylformamide was stirred and heated at 120° for 4 hours. The solvent was removed in vacuo on the steam bath, and 75 ml. of water added to the residue. The oil was extracted with ethyl acetate and the crude product precipitated as the hydrochloride by the addition of hydrogen chloride. On crystallization from acetone, 1.5 g. of 8-chlorodibenzothiophene-3-acetic acid 2-dimethylaminoethyl ester hydrochloride, m.p. 179°-181°, was obtained.

Workup

  1. additionA mixture of 2.76 g
  2. temperatureheated at 120° for 4 hours
  3. customThe solvent was removed in vacuo on the steam bath, and 75 ml
  4. additionof water added to the residue
  5. extractionThe oil was extracted with ethyl acetate
  6. customthe crude product precipitated as the hydrochloride by the addition of hydrogen chloride
  7. customOn crystallization from acetone, 1.5 g

Sources & evidence

ORD record
ord-c88c0a5218804a50aafec4f596fdd1d2
Source dataset
uspto-grants-1982_06
Patent number
US04334078

Reaction notes

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