Water → HCID 53647039, compound

HRID 486874Notes

Reaction equation

HRID 486874 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]=[C:11](Cl)[CH2:12][Cl:13])=[C:4]([F:15])[CH:3]=1.[CH3:16][O:17][C:18](=[O:28])[C:19]1[CH2:27][CH2:26][CH2:25][CH2:24][C:20]=1[C:21](N)=[O:22].C(N(CC)CC)C.[OH2:36]>C1C=CC=CC=1>[CH3:16][O:17][C:18](=[O:28])[C:19]1[CH2:27][CH2:26][CH2:25][CH2:24][C:20]=1[C:21]([N:10]([C:11](=[O:36])[CH2:12][Cl:13])[C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=1[F:15])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15334633Methyl 2-carbamoylcyclohex-1-ene-1-carboxylateHCID 19096775HCID 19096775, compound

Product 1

HCID 53647039HCID 53647039, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

First, 1.47 g of N-(4-chloro-2-fluoro-5-methoxyphenyl)-2-chloroacetimidoylchloride and 1.00 g of 3,4,5,6-tetrahydrophthalamic acid monomethyl ester were dissolved in 20 ml of benzene, and 570 mg of triethylamine dissolved in 5 ml of benzene was added to the solution at room temperature. After that the stirring was continued for 1.5 hr at 60° C. After letting the reaction liquid stand to cool the same, it was poured into iced water, and then the organic layer was separated therefrom. The organic layer was washed first with water and then with saturated brine, and then dried by using anhydrous magnesium sulfate. The solvent was concentrated, and then methanol was added to the residue. The produced crystals were filtered out, then washed with methanol, and then dried to obtain 1.18 g of N-(2-chloroacetyl)-N-(4-chloro-2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalamic acid methyl ester. The melting point was 109° C.

Workup

  1. additionwas added to the solution at room temperature
  2. customthe reaction liquid stand
  3. temperatureto cool the same, it
  4. customthe organic layer was separated
  5. washThe organic layer was washed first with water
  6. dry with materialwith saturated brine, and then dried
  7. concentrationThe solvent was concentrated
  8. additionmethanol was added to the residue
  9. filtrationThe produced crystals were filtered out
  10. washwashed with methanol
  11. customdried

Sources & evidence

ORD record
ord-816037ac9798499fb35adc60a8bc5166
Source dataset
uspto-grants-1994_03
Patent number
US05292922

Reaction notes

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