3-Amino-4-hydroxybenzoic acid → 2-(4-Carbomethoxyphenyl)-5-carboxybenzoxazole

HRID 2419531Notes

Reaction equation

HRID 2419531 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10](Cl)(Cl)Cl)=[CH:6][CH:5]=1.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[OH:25])[C:19]([OH:21])=[O:20]>>[C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:25][C:24]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=3[N:15]=2)=[CH:6][CH:5]=1)([O:2][CH3:1])=[O:14]

Participants

3

Reactant 2

HCID 650833-Amino-4-hydroxybenzoic acidHCID 84661Methyl 4-(trichloromethyl)benzoate

Product 1

HCID 203138222-(4-Carbomethoxyphenyl)-5-carboxybenzoxazole

Conditions

Temperature
200 °C

Procedure

In the apparatus described in Example 1, 12.7 g of 4-trichloromethylbenzoic acid methyl ester (0.05 mol) and 7.5 g of 3-amino-4-hydroxybenzoic acid (0.05 mol) were mixed and heated for 6 hours at 200° C. The reaction product after grinding in a mortar was extracted twice with 100 ml of CHCl3 and then, after drying, twice with 100 ml of water. 9.2 g of raw product remained, melting at 275° to 284° C (62% of the theory). After two recrystallizations with dimethyl formamide plus active charcoal and dimethylsulfoxide, the melting point was 291° to 293° C.

Workup

  1. additionwere mixed
  2. customThe reaction product after grinding in a mortar
  3. extractionwas extracted twice with 100 ml of CHCl3
  4. dry with materialafter drying, twice with 100 ml of water
  5. customAfter two recrystallizations with dimethyl formamide plus active charcoal and dimethylsulfoxide

Sources & evidence

ORD record
ord-bf3bc6f118534e35b09056df7eca003b
Source dataset
uspto-grants-1978_08
Patent number
US04107169

Reaction notes

Loading…