Hydrochloric Acid → HCID 19081186, compound

HRID 963503Notes

Reaction equation

HRID 963503 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:17].Cl>O1CCCC1.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([NH:5][C:16](=[O:17])[O:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 115683-AminophenolHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 19081186HCID 19081186, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-hydroxyaniline (2.0 g) and pyridine (3.3 ml) in tetrahydrofuran was stirred at 0° C. and then p-nitrophenyl chloroformate (3.88 g) was added, stirred at the same temperature for 5 hours. Ethyl acetate and 1N HCl were added to the reaction mixture, and the organic layer was separated, washed with water, dried over magnesium sulfate, and evaporated in vacuo. The yellow powder was washed with ethyl acetate to afford 4-nitro-phenyl N-(3-hydroxyphenyl)carbamate (554 mg).

Workup

  1. stirringstirred at the same temperature for 5 hours
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washThe yellow powder was washed with ethyl acetate

Sources & evidence

ORD record
ord-dc2763615a2f4f1b861c63c16107805b
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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