Water → HCID 52951166, compound

HRID 508601Notes

Reaction equation

HRID 508601 reaction equation
C(OC(=O)[NH:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:17]2[CH:22]=[CH:21][C:20]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:19][CH:18]=2)[N:7]=1)C.[OH-].[Na+].O>CCO>[NH2:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:8]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:24])(=[O:25])=[O:26])=[CH:19][CH:18]=2)[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 52951165HCID 52951165, compound

Product 1

HCID 52951166HCID 52951166, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of an ethyl carbamate 5 (0.39 g, 1 mmol) in EtOH (10 mL) was added 10% NaOH solution (3.2 mL) at room temperature. The reaction mixture was refluxed for 5 hours. The reaction mixture was cooled to room temperature and water was added. The resulting white precipitate was filtered and washed with water thoroughly to give the titled compound (0.22 g, 70%) as a white solid. mp 286.3-290.2° C. 1H NMR (DMSO-d6): δ 7.70 (d, J=9 Hz, 2H), 7.43-7.20 (m, 9H), 5.89 (s, 1H), 5.17 (br s, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. filtrationThe resulting white precipitate was filtered
  3. washwashed with water thoroughly

Sources & evidence

ORD record
ord-5110ce518d6843c18f7ca34af9d7272a
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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