Phosgene → HCID 18707188, compound

HRID 1489240Notes

Reaction equation

HRID 1489240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([NH2:23])[CH:17]=3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[C:31](Cl)(Cl)=[O:32]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]4[O:22][C:31](=[O:32])[NH:23][C:18]=4[CH:17]=3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 18707379HCID 18707379, compound

Product 1

HCID 18707188HCID 18707188, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of tetrahydrofuran was dissolved 300 mg of 2-(3,4-dimethoxyphenyl)-4-(3-amino-4-hydroxyphenyl)thiazole. Thereto was added 0.46 ml of triethylamine at room temperature. The mixture was stirred at the same temperature for 30 minutes. 100 mg of phosgene was blown thereinto, and the resulting mixture was stirred for 2 hours. The solvent was distilled off. The residue was washed with diethyl ether, followed by filtration to collect crystals. The crystals were recrystallized from methanol to obtain 50 mg of 2-(3,4-dimethoxyphenyl)-4-(benzoxazol-2-on-5-yl)thiazole as a white powder.

Workup

  1. stirringthe resulting mixture was stirred for 2 hours
  2. distillationThe solvent was distilled off
  3. washThe residue was washed with diethyl ether
  4. filtrationfollowed by filtration
  5. customto collect crystals
  6. customThe crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-e1c7128d5520464086478fb6fdd0c302
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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