Water → HCID 86744736, compound

HRID 1085512Notes

Reaction equation

HRID 1085512 reaction equation
CO[C:3]1[CH:11]=[C:10](N)[C:9](Cl)=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N1C=CN=C1)([N:16]1C=CN=C1)=O.[CH3:26][N:27]([CH:31]1[CH2:33][CH2:32]1)[CH2:28][CH2:29]N.O>O1CCCC1>[CH3:26][N:27]([CH:31]1[CH2:33][CH2:32]1)[CH2:28][CH2:29][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:16])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 9989245N-(2-aminoethyl)-N-methylcyclopropanamine

Product 1

HCID 86744736HCID 86744736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

15.6 g of N-acetyl-N'-methylcyclopropylethylenediamine are refluxed during two hours with 80 ml of 15% hydrochloric acid. The solution is then saturated with sodium hydroxide, extracted with ethyl ether, the organic extract is dried and evaporated at 20° C./15 mm/Hg. Gas-chromatographically pure N-acetyl-N'-methyl-N'-cyclopropylethylene is thus obtained. 8.06 g (0.04 mole) of 2-methoxy-4-amino-5-chlorobenzoic acid and 7.12 g (0.044 mole) of carbonyldiimidazole are suspended in 80 ml of tetrahydrofuran and kept at 30° C. until the gas evolution stopped. A solution containing 5.7 g (0.05 mole) of N-methyl-N-cyclopropylethylenediamine in 15 ml of tetrahydrofuran is then slowly added at room temperature, and thereafter the temperature is kept at 50° C. for one hour. After cooling down, the mixture is poured into water, the solid is removed by filtration and crystallized from alcohol, thus obtaining 9.6 (80.6%) of 2-methoxy-4-amino-5-chloro-N-(2-(methylcyclopropylamino)ethyl-benzamide having a melting point of 164°-5° C. Hydrochloride, m.p. 130°-2° C.

Workup

  1. customkept at 30° C. until the gas evolution
  2. additionis then slowly added at room temperature
  3. temperatureAfter cooling down
  4. customthe solid is removed by filtration
  5. customcrystallized from alcohol

Sources & evidence

ORD record
ord-cf19fce0bac24d1489ba918cc6d825f2
Source dataset
uspto-grants-1991_04
Patent number
US05010108

Reaction notes

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