Triethylamine → HCID 20196821, compound

HRID 652756Notes

Reaction equation

HRID 652756 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([S:13](=[O:18])(=[O:17])[N:14]([CH3:16])[CH3:15])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH:34]1([N:37]2[CH2:41][CH2:40][CH2:39][CH:38]2[CH2:42][NH2:43])[CH2:36][CH2:35]1>O>[CH:34]1([N:37]2[CH2:41][CH2:40][CH2:39][CH:38]2[CH2:42][NH:43][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([S:13](=[O:18])(=[O:17])[N:14]([CH3:16])[CH3:15])[C:10]([NH2:12])=[CH:11][C:3]=2[O:2][CH3:1])[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 20196828HCID 20196828, compoundHCID 54368144HCID 54368144, compound

Product 1

HCID 20196821HCID 20196821, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

68.5 g of 2-methoxy-4-amino-5-dimethylsulphamoyl benzoic acid (0.25 mole), 740 ml of water and 25.4 g of triethylamine (0.25 mole) are placed in a 2 liter flask fitted with an agitator, a thermometer, a condenser and a dropping funnel. The solution is cooled to about 0° C, and 34.1 g of isobutyl chloroformate (0.25 mole) is poured in drop by drop. The mixture is reacted for 40 minutes at room temperature then cooled, and 42 g of 1-cyclopropyl-2-aminomethylpyrrolidine is added drop by drop, while the temperature is kept between 0° and +5° C. The medium is reacted for 3 hours at room temperature, then the solution is evaporated dry under vacuum. The residue is dissolved in 250 ml of water and 50 ml of hydrochloric acid. The solution is extracted twice with 125 ml of methylene chloride, which is eliminated. The aqueous phase is made alkaline with 70 ml of soda lye.

Workup

  1. customfitted with an agitator
  2. customThe mixture is reacted for 40 minutes at room temperature
  3. temperaturethen cooled
  4. customis kept between 0° and +5° C
  5. customThe medium is reacted for 3 hours at room temperature
  6. customthe solution is evaporated
  7. customdry under vacuum
  8. dissolutionThe residue is dissolved in 250 ml of water
  9. extractionThe solution is extracted twice with 125 ml of methylene chloride, which

Sources & evidence

ORD record
ord-7d71e0abac4a438e88e13cd6cbc26d3b
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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