Dimethylformamide → HCID 14400513, compound

HRID 1073674Notes

Reaction equation

HRID 1073674 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CN(C)C=O.C(Cl)([Cl:22])=O>C1(C)C=CC=CC=1.O>[CH:8]1([N:14]2[C:4](=[O:5])[CH2:3][CH:2]([Cl:22])[C:1]2=[O:7])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6371Phosgene2×HCID 7923Maleic AnhydrideHCID 7965Cyclohexylamine

Product 1

HCID 14400513HCID 14400513, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Using the same apparatus as described in Example 1, 34.7 g (0.354 mole) of maleic anhydride was dissolved in 260 g of toluene and 34.7 g (0.350 mole) of cyclohexylamine was added to the resulting solution over 0.5 hour at 10°-50° C. After stirring the reaction mixture for 0.5 hour at the same temperature, 1.27 g (0.0175 mole) of dimethylforamide was added and 38.1 g (0.385 mole) of phosgene was then blown into the reaction mixture over 4 hours at 35°-40° C. After raising the temperature to 70°-75° C., nitrogen gas was blown through the reaction mixture for 2 hours to carry out phosgene degassing and water was added to wash the reaction mixture. The reaction mixture was dried. Solvent was removed and the residue was vacuum distilled at 138°-140° C., 1-2 mmHg. The N-Cyclohexylmonochlorosuccinimide thus obtained (72.7 g, 96.6% of theoretical yield) had a melting point of 63°-64° C.

Workup

  1. additionwas added
  2. temperatureAfter raising the temperature to 70°-75° C.
  3. additionwas added
  4. washto wash the reaction mixture
  5. customThe reaction mixture was dried
  6. customSolvent was removed
  7. distillationdistilled at 138°-140° C.

Sources & evidence

ORD record
ord-6ef161868cb54683abeebdeed843d71f
Source dataset
uspto-grants-1990_11
Patent number
US04970323

Reaction notes

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