Carbon Tetrachloride → HCID 21557902, compound

HRID 328296Notes

Reaction equation

HRID 328296 reaction equation
O1CCCC1.C(Cl)(Cl)(Cl)Cl.[Cl:11][C:12]1[CH:30]=[CH:29][CH:28]=[C:14]2[C:15]([N:17]([C:20]([CH:25]([CH3:27])[CH3:26])([CH3:24])[C:21]([NH2:23])=O)[C:18](=[O:19])[C:13]=12)=[O:16].C(N(CC)CC)C>[Ti](Cl)(Cl)(Cl)Cl.O>[Cl:11][C:12]1[CH:30]=[CH:29][CH:28]=[C:14]2[C:15]([N:17]([C:20]([CH:25]([CH3:27])[CH3:26])([CH3:24])[C:21]#[N:23])[C:18](=[O:19])[C:13]=12)=[O:16]

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8028Tetrahydrofuran3×HCID 8471TriethylamineHCID 21441267HCID 21441267, compound

Product 1

HCID 21557902HCID 21557902, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 60 ml. dry tetrahydrofuran, stirred and cooled to 0° C. is added dropwise 11.5 ml. titanium tetrachloride in 15 ml. dry carbon tetrachloride. To this cold mixture is added 8.82 grams of α-(3-chlorophthalimido)-α-isopropyl-α-methylacetamide in 50 ml. dry tetrahydrofuran, followed by 12.3 grams triethylamine in 20 ml. dry tetrahydrofuran. The reaction mixture is allowed to warm slowly to room temperature and kept overnight. Water is then added cautiously to the mixture while it is extracted three times with ether. The combined extracts are washed with water, dried, and evaporated. The residue is crystallized from ether-hexane to give 6.1 grams of the nitrile, melting point 71° C. to 72° C.

Workup

  1. additionis added dropwise 11.5 ml
  2. temperatureto warm slowly to room temperature
  3. extractionis extracted three times with ether
  4. washThe combined extracts are washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is crystallized from ether-hexane

Sources & evidence

ORD record
ord-776f25da479c434ea970b2d9306a4914
Source dataset
uspto-grants-1977_04
Patent number
US04017299

Reaction notes

Loading…