4-Chlorobenzotrichloride → Benzoxazole, 5-chloro-2-(4-chlorophenyl)-

HRID 2419528Notes

Reaction equation

HRID 2419528 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)(Cl)Cl)=[CH:4][CH:3]=1.Cl.[NH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[OH:21]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:21][C:15]3[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=3[N:13]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 212774-ChlorobenzotrichlorideHCID 165320Phenol, 2-amino-4-chloro-, hydrochloride (1:1)

Product 1

HCID 548468Benzoxazole, 5-chloro-2-(4-chlorophenyl)-

Procedure

Compound XIV was prepared as in Example 12 at 180° C from p-chlorobenzotrichloride and 2-amino-4-chlorophenol hydrochloride, and purified through a preheated aluminum trioxide column: 16 g of raw product, M.P. 178°-183° C (61% of the theory). Upon recrystallization from benzene: M.P. 190°-192° C.

Workup

  1. custompurified through a preheated aluminum trioxide column
  2. customUpon recrystallization from benzene

Sources & evidence

ORD record
ord-47fcb5c3ddfc43a4a3f79153bd75a1ad
Source dataset
uspto-grants-1978_08
Patent number
US04107169

Reaction notes

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