Triethylamine → HCID 20196878, compound

HRID 652763Notes

Reaction equation

HRID 652763 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([Cl:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH:29]1([N:35]2[CH2:39][CH2:38][CH:37]([NH2:40])[CH:36]2[CH3:41])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CC(C)=O.O>[CH:29]1([N:35]2[CH2:39][CH2:38][CH:37]([NH:40][C:5](=[O:7])[C:4]3[CH:8]=[C:9]([Cl:13])[C:10]([NH2:12])=[CH:11][C:3]=3[O:2][CH3:1])[CH:36]2[CH3:41])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 20196854HCID 20196854, compound

Product 1

HCID 20196878HCID 20196878, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

8 g of 2-methoxy-4-amino-5-chlorobenzoic acid (0.040 mole), 50 ml of acetone and 4 g of triethylamine (0.040 mole) are placed in a 250 ml flask fitted with an agitator, a thermometer and a dropping funnel. The suspension is cooled and 5.5 g of isobutyl chloroformate (0.040 mole) is added drop by drop between 0° and +5° C. The reaction medium is agitated for 45 minutes with the temperature kept between 0° and +5° C., then 8 g of 1-cyclohexyl-methyl-3-aminopyrrolidine (0.044 mole) is added drop by drop. The reaction is allowed to continue for 2 hours at room temperature, then 80 ml of water is added and the acetone is expelled. The product crystallises in the residual water. It is filtered and re-dissolved in 150 ml of water and 5 ml of concentrated hydrochloric acid. The solution is filtered with charcoal and the filtrate is made alkaline with 10 ml of ammonia (density 0.91). The viscous precipitate is decanted and dissolved in 80 ml of water and 5 ml of hydrochloric acid. The product is dissolved and the hydrochloride is precipitated very rapidly. It is drained, washed with water and dried at 50° C. 10.4 g of product is obtained and is dissolved hot in 100 ml of water. The solution is rendered alkaline with 10 ml of soda lye. The oily precipitate is crystallised by cooling. It is drained, washed with water and dried in an oven at 50° C.

Workup

  1. customfitted with an agitator
  2. temperatureThe suspension is cooled
  3. customkept between 0° and +5° C.
  4. waitto continue for 2 hours at room temperature
  5. customThe product crystallises in the residual water
  6. filtrationIt is filtered
  7. dissolutionre-dissolved in 150 ml of water
  8. filtrationThe solution is filtered with charcoal
  9. customThe viscous precipitate is decanted
  10. dissolutiondissolved in 80 ml of water
  11. dissolutionThe product is dissolved
  12. customthe hydrochloride is precipitated very rapidly
  13. washwashed with water
  14. customdried at 50° C

Sources & evidence

ORD record
ord-060100f761034751b7a1c8213cd0e342
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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