Phosgene → HCID 14772402, compound

HRID 2073714Notes

Reaction equation

HRID 2073714 reaction equation
[N:1]1[O:2][C:3]2[CH2:4][CH2:5][CH2:6][CH:7]3[C:16]=2[C:15]=1[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:8]3.[C:17](Cl)([Cl:19])=[O:18].C(N(CC)CC)C>ClCCl.C1C=CC=CC=1>[N:1]1[O:2][C:3]2[CH2:4][CH2:5][CH2:6][CH:7]3[C:16]=2[C:15]=1[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:8]3[C:17]([Cl:19])=[O:18]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 135618014HCID 135618014, compound

Product 1

HCID 14772402HCID 14772402, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 50 ml of dichloromethane was dissolved 4.08 g of 4,5,5a,6-tetrahydro-3H-isoxazolo[5,4,3-kl]acridine. Phosgene in benzene (26 ml of 12.5% phogene in benzene) was then added all in one portion. This solution was then chilled with an ice/water bath as a solution of triethylamine (2.92 g) in 20 ml of dichloromethane was added dropwise. After the addition was complete (30 minutes), the reaction mixture was washed with dilute hydrochloric acid and then dried and concentrated. The residue obtained in this manner was recrystallized from dichloromethane/hexane to give 3.66 g of product, m.p. 189° C. (d).

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. custom(30 minutes)
  4. washthe reaction mixture was washed with dilute hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. customThe residue obtained in this manner
  8. customwas recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-aa7002113a5f4d3790330492b8b2e960
Source dataset
uspto-grants-1990_04
Patent number
US04920117

Reaction notes

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