4-Chlorobenzoyl chloride → HCID 23453038, compound

HRID 1277665Notes

Reaction equation

HRID 1277665 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 20463409Ethyl 4-(2-aminoethyl)benzeneacetate

Product 1

HCID 23453038HCID 23453038, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

8.3 g 4-Chlorobenzoyl chloride are added dropwise at 5°-10° C., within the course of 10 minutes, to a solution of 11.0 g ethyl 4-(2-aminoethyl)-phenylacetate in 90 ml anhydrous pyridine. The reaction mixture is then stirred for 90 minutes at 10° C., subsequently allowed to warm up to 20° C. and thereafter warmed to 40°-45° C. for 30 minutes. The reaction mixture is then cooled and stirred into 900 ml ice water, a solid precipitate thereby being obtained. This is filtered off with suction and washed with water. There are obtained 14.5 g (94% of theory) of crude product which is recrystallized from isopropanol to give 10.9 g (70% of theory) ethyl 4-[2-(4-chlorobenzamido)-ethyl]-phenylacetate; m.p. 118°-119° C.

Workup

  1. temperatureto warm up to 20° C.
  2. temperaturewarmed to 40°-45° C. for 30 minutes
  3. temperatureThe reaction mixture is then cooled
  4. customa solid precipitate thereby being obtained
  5. filtrationThis is filtered off with suction
  6. washwashed with water
  7. customThere are obtained 14.5 g (94% of theory) of crude product which
  8. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-5a0d52d38e4c4722be3071ad79ac0536
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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