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Triethylamine → N-(1-cyclohexylmethyl-2-pyrrolidinyl-methyl)-2,3-dimethoxy-5-sulphamoyl benzamide

HRID 652767
Notes
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Reaction equation

HRID 652767 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH:31]1([CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH:39]2[CH2:43][NH2:44])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>CC(C)=O.O>[CH:31]1([CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH:39]2[CH2:43][NH:44][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:10]=[C:11]([O:12][CH3:13])[C:3]=2[O:2][CH3:1])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 30176982,3-Dimethoxy-5-sulphamoylbenzoic acidHCID 21268496[1-(Cyclohexylmethyl)pyrrolidin-2-yl]methanamine

Product 1

HCID 54427560N-(1-cyclohexylmethyl-2-pyrrolidinyl-methyl)-2,3-dimethoxy-5-sulphamoyl benzamide

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 962WaterSolvent

Procedure

26.1 g of 2,3-dimethoxy-5-sulphamoyl-benzoic acid (0.10 mole), 40 ml of water, 200 ml of acetone and 10.1 g of triethylamine (0.10 mole) are placed in a 500 ml flask fitted with an agitator, a thermometer and a dropping funnel. The solution is cooled to between 0° and +5° C. and 10.9 g of ethyl chloroformate (0.10 mole) is added drop by drop. It is agitated for 1 hour 30 with the temperature kept at about +5° C., then 19.6 g of 1-cyclohexylmethyl-2-aminomethyl pyrrolidine (0.10 mole) is added drop by drop. A precipitate forms progressively as more and more is added. The reaction medium is then agitated at room temperature, after which it is left to stand. The crystals are filtered, washed three times with water then with 100 ml of 10% ammonia and dried in an oven at 50° C. 50 g is obtained.

Workup

  1. customfitted with an agitator
  2. temperatureThe solution is cooled to between 0° and +5° C.
  3. customkept at about +5° C.
  4. additionA precipitate forms progressively as more and more is added
  5. stirringThe reaction medium is then agitated at room temperature
  6. waitafter which it is left
  7. filtrationThe crystals are filtered
  8. washwashed three times with water
  9. dry with materialwith 100 ml of 10% ammonia and dried in an oven at 50° C
  10. custom50 g is obtained

Sources & evidence

ORD record
ord-a4222df6281d437182c1142fee59b460
Source dataset
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04673686

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes