Pyridine → HCID 20437363, compound

HRID 1733534Notes

Reaction equation

HRID 1733534 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:19][C:20]([F:50])([F:49])[C:21]([N:23]([C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:22]>ClCCl>[F:19][C:20]([F:49])([F:50])[C:21]([N:23]([C:40]1[CH:48]=[CH:47][C:43]([C:44]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)=[O:45])=[CH:42][CH:41]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2337BenzocaineHCID 20437337HCID 20437337, compound

Product 1

HCID 20437363HCID 20437363, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 1.65 g. of ethyl p-aminobenzoate and 1.6 ml. of pyridine in 5 ml. of dichloromethane at 0° C. is added a solution of 4.75 g. of p-(2,2,2-trifluoro-N-hexadecylacetamido)benzoyl chloride in 10 ml. of dichloromethane. After 20 hours at ambient temperature the solution is diluted with dichloromethane and washed with water and sodium bicarbonate solution. The residue obtained on evaporation of solvent is recrystallized from hexane-ether to give a white, crystalline solid, m.p. 91°-93° C.

Workup

  1. washwashed with water and sodium bicarbonate solution
  2. customThe residue obtained on evaporation of solvent
  3. customis recrystallized from hexane-ether
  4. customto give a white, crystalline solid, m.p. 91°-93° C.

Sources & evidence

ORD record
ord-df855096beb0442ba0b1824526cde3ed
Source dataset
uspto-grants-1980_12
Patent number
US04242273

Reaction notes

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