Ammonia → HCID 86741588, compound

HRID 652775Notes

Reaction equation

HRID 652775 reaction equation
[CH3:1][O:2][C:3]1[C:11]([S:12](=[O:15])(=[O:14])[NH2:13])=[C:10]([NH2:16])[C:9]([CH3:17])=[CH:8][C:4]=1[C:5]([OH:7])=O.Cl[C:19](OCC)=O.[CH:24]1([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2(C)[CH2:36][NH2:37])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.N>O.Cl.C(N(CC)CC)C.CC(C)=O>[CH:24]1([N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[CH:36]([CH3:19])[NH:37][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([CH3:17])[C:10]([NH2:16])=[C:11]([S:12](=[O:15])(=[O:14])[NH2:13])[C:3]=2[O:2][CH3:1])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 10928Ethyl chloroformateHCID 54119204HCID 54119204, compoundHCID 54502136HCID 54502136, compound

Product 1

HCID 86741588HCID 86741588, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

6.5 g of 2-methoxy-4-amino-5-methyl sulphamoyl benzoic acid, 75 ml of acetone, 14 ml of water and 3.5 ml of triethylamine (density 0.726) are placed in a 250 ml flask fitted with an agitator, a thermometer, a condenser and a dropping funnel. The solution is cooled to between 0° and +5° C. and 2.7 g of ethyl chloroformate is added drop by drop. The reaction medium is agitated for 45 minutes at room temperature then cooled to 0° C. again. 6.8 g of 1-cycloheptyl methyl-2-amino methyl pyrrolidine is added drop by drop. The medium is reacted for 2 hours then left to stand. The solvents are expelled and the solid residue dissolved in 50 ml of water and 20 ml of hydrochloric acid (density 1.18). The suspension obtained is made alkaline with ammonia. It is extracted 3 times with 50 ml of methylene chloride. The organic phase is washed twice with 50 ml of water, dried over magnesium sulphate and filtered. The filtrate is evaporated to dryness under vacuum. The residue is dissolved in 80 ml of water and 20 ml of hydrochloric acid (density 1.18). The hydrochloride crystallises. It is drained, washed with water and dried in an oven at 50° C.

Workup

  1. customfitted with an agitator
  2. temperatureThe solution is cooled to between 0° and +5° C.
  3. temperaturethen cooled to 0° C. again
  4. customThe medium is reacted for 2 hours
  5. waitthen left
  6. customThe suspension obtained
  7. extractionIt is extracted 3 times with 50 ml of methylene chloride
  8. washThe organic phase is washed twice with 50 ml of water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customThe filtrate is evaporated to dryness under vacuum
  12. dissolutionThe residue is dissolved in 80 ml of water
  13. customThe hydrochloride crystallises
  14. washwashed with water
  15. customdried in an oven at 50° C.

Sources & evidence

ORD record
ord-ce9e4f3e2d2044e7a16d701530368b17
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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