Chloride → beta-Dimethylaminoethyl 3-chloro-4-benzyloxyphenylacetate hydrochloride

HRID 27605Notes

Reaction equation

HRID 27605 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:16][C:17]([OH:19])=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].S(Cl)(Cl)=O.[CH3:25][N:26]([CH2:28][CH2:29]O)[CH3:27]>C1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:16][C:17]([O:19][CH2:29][CH2:28][N:26]([CH3:27])[CH3:25])=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 312Chloride2×HCID 79022-(Dimethylamino)ethanolHCID 24386Thionyl ChlorideHCID 91676Benzofenac

Product 1

HCID 23343310beta-Dimethylaminoethyl 3-chloro-4-benzyloxyphenylacetate hydrochlorideYield 131.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
5 °C

Procedure

6.15 grams of 3-chloro-4-benzyloxyphenylacetic acid was converted into the corresponding chloride by treatment with 15 ml of thionyl chloride in 50 ml of benzene. A solution comprising 1.85 grams of dimethylaminoethanol in 10 ml of benzene was slowly added at 20° C. to the chloride solution. The mixture was then permitted to stand for 2 hours at that temperature and then cooled to 5° C., so yielding a precipitate which was filtered and washed with benzene. Two crystallizations from ethylacetate-isopropyl alcohol (1:1) yielded 5.6 grams (68.4%) of β-dimethylaminoethyl 3-chloro-4-benzyloxyphenylacetate hydrochloride, m.p. 138°-140° C.

Workup

  1. customso yielding a precipitate which
  2. filtrationwas filtered
  3. washwashed with benzene
  4. customTwo crystallizations from ethylacetate-isopropyl alcohol (1:1)

Sources & evidence

ORD record
ord-5a19c020631c4af9a138822f925c795b
Source dataset
uspto-grants-1980_09
Patent number
US04221919

Reaction notes

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