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

HRID 1582205Notes

Reaction equation

HRID 1582205 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-1563da5dfcc843afa32438c1b95f41bf
Source dataset
uspto-grants-2004_05
Patent number
US06734194B2

Reaction notes

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