N-methyl-2-pyrrolidone → HCID 86747391, compound

HRID 258063Notes

Reaction equation

HRID 258063 reaction equation
CN1C(=O)CCC1.[Cl-].[Cl-].[Ca+2].[NH2:11][C:12]1[CH:13]=[C:14]([C:21]([Cl:23])=[O:22])[CH:15]=[C:16]([CH:20]=1)[C:17]([Cl:19])=[O:18]>CC(N(C)C)=O.[Li+].[Br-].OP(O)(O)=O.C1COCC1>[ClH:19].[NH2:11][C:12]1[CH:20]=[C:16]([C:17]([Cl:19])=[O:18])[CH:15]=[C:14]([CH:13]=1)[C:21]([Cl:23])=[O:22]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidone2×HCID 5284359Calcium ChlorideHCID 19021055HCID 19021055, compound

Product 1

HCID 86747391HCID 86747391, compound

Reagents, catalysts & solvents 1

HCID 86747393HCID 86747393, compoundSolvent

Procedure

To a 500 ml resin kettle with a stainless egg beater type stirrer fitted with a nitrogen inlet and CaSO4 tube outlet was added 200 ml of NMP and 15.6 g of CaCl2. It was warmed with until all of the salt dissolved. The resin kettle was immersed in an ice bath, and was stirred for 30 min in the ice bath to ensure low temperature. To this was added 6.76 g of 5-aminoisophthaloyl chloride and then the ice bath was removed, and stirring was continued for 2 hrs. The solution was poured into water in a blender, and a white opaque precipitate was formed. The precipitate was collected by filtration after the solution was centrifuged at 13,000 rpm for 4 hours. After air drying 6.0 g of the product was obtained. NMR and TGA analysis indicated that NMP was still present. 1H NMR (d-DMF): 8.0,8.5, 8.55, 8.65, 8.95, 11.1. 13C NMR (d-DMF): 122.8, 123.8, 124.3, 124.6, 125.0, 125.6, 125.7, 126.2, 132.8, 136.5, 136.7, 140.9, 166.2, 167.5. GPC molecular weight in DMAc/LiBr/H3PO4 /THF: Mn=46,000, PD=2.53 (against polystyrene standard).

Workup

  1. temperatureIt was warmed with until all of the salt
  2. dissolutiondissolved
  3. customThe resin kettle was immersed in an ice bath
  4. customthe ice bath was removed
  5. additionThe solution was poured into water in a blender
  6. customa white opaque precipitate was formed
  7. filtrationThe precipitate was collected by filtration after the solution
  8. waitwas centrifuged at 13,000 rpm for 4 hours
  9. dry with materialAfter air drying 6.0 g of the product
  10. customwas obtained

Sources & evidence

ORD record
ord-97af2b897bbc46218d2205e4c1eb2ef0
Source dataset
uspto-grants-1993_11
Patent number
US05264543

Reaction notes

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