Ammonia → (4-Chlorophenyl)[3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl]methanone

HRID 2229278Notes

Reaction equation

HRID 2229278 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]4([C:22]5[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=5)OCC[O:18]4)=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1.N>Cl.CO>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:17]([C:14]2[CH:15]=[CH:16][C:11]3[C:12]([CH:13]=2)=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:9][N:10]=3)=[O:18])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 23248654HCID 23248654, compound

Product 1

HCID 22136476(4-Chlorophenyl)[3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl]methanoneYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of intermediate (6-a) (30 g) in HCl 3 N (220 ml) and methanol (165 ml) was stirred at 100° C. for 5 hours. The mixture was poured into ice and basified with NH3 (aq.). The precipitate was filtered off, washed with water and diethyl ether and dried, yielding 24.9 g (93%) of (4-chlorophenyl)[3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl]methanone (interm. 6-b). The product was used without further purification.

Workup

  1. additionThe mixture was poured into ice
  2. filtrationThe precipitate was filtered off
  3. washwashed with water and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-410a8cb09be5485aab27fe7feb0d7fa1
Source dataset
uspto-grants-2002_07
Patent number
US06420387B1

Reaction notes

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