Acetic Acid → HCID 178518390, compound

HRID 1176036Notes

Reaction equation

HRID 1176036 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].[OH-].[Na+].[O-:14][C:15]#[N:16].[Na+].C(O)(=O)C>O.O1CCOCC1>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:15]([OH:14])[N:16]=[C:4]2[OH:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2×HCID 72911Benzoic acid, 2-amino-5-iodo-HCID 517096Sodium Cyanate

Product 1

HCID 178518390HCID 178518390, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of commercially available 2-amino-5-iodobenzoic acid (1 g, 3.80 mmol) in water (5 mL) and 2N aqueous sodium hydroxide (1.9 mL, 3.80 mmol), was added sodium cyanate (272 mg, 4.18 mmol). The reaction mixture was then diluted with dioxane (3 mL). The reaction mixture was maintained at approximate pH 6-7 over the course of 3 hours, by the addition of acetic acid (228 μl). The mixture was stirred at room temperature for 18 hours then cooled to 0 C. The pH of the reaction was adjusted to 13-14 with the addition of 6N aqueous sodium hydroxide (1 mL), then the mixture was heated at 55 C for 3.5 hours. The reaction mixture was cooled to 0 C and the precipitate was collected, washed with water, then dried by lyophilization to give 6-iodo-quinazoline-2,4-diol as a lavender solid, (849 mg, 78%). HNMR (500 MHz, DMSO) 6.72 (d, 1H), 7.53 (d, 1H), 7.95 (s, 1H), LCMS m/e 286.98 (M+H).

Workup

  1. temperaturethen cooled to 0 C
  2. temperaturethe mixture was heated at 55 C for 3.5 hours
  3. temperatureThe reaction mixture was cooled to 0 C
  4. customthe precipitate was collected
  5. washwashed with water
  6. customdried by lyophilization

Sources & evidence

ORD record
ord-31bae99002c842dabd199dde0afbc1d1
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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