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

HRID 840159Notes

Reaction equation

HRID 840159 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-c9d90fc45dbc431590dc4800f94b6caf
Source dataset
uspto-grants-2002_04
Patent number
US06365600B1

Reaction notes

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