Tetrahydrofuran → HCID 67215476, compound

HRID 1983114Notes

Reaction equation

HRID 1983114 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[NH2:23])C(O)=O.C1C[O:27][CH2:26]C1>>[N:8]1([C:1]([C:16]2[CH:20]=[CH:21][C:22]3[NH:23][C:26](=[O:27])[NH:13][C:14]=3[CH:15]=2)=[O:2])[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 692633,4-Diaminobenzoic acid

Product 1

HCID 67215476HCID 67215476, compoundYield 66%

Procedure

To a solution of 1,1′-carbonyl-diimidazole (11.7 g, 72.3 mmol) in THF (500 mL) was added 3,4-diaminobenzoic acid (5.00 g, 32.9 mmol) and stirred for 3 days at ambient temperature. The reaction mixture was concentrated and stirred for 30 min at 80° C. in water (100 mL). The resulting suspension was then cooled to ambient temperature and the mixture was filtered off and washed with water (2×50 mL) to afford the title compound (4.94 g, 66%) which was obtained as a white solid. MS: m/e=229.3 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringstirred for 30 min at 80° C. in water (100 mL)
  3. temperatureThe resulting suspension was then cooled to ambient temperature
  4. filtrationthe mixture was filtered off
  5. washwashed with water (2×50 mL)

Sources & evidence

ORD record
ord-f5a387f9d81a44e89f749cc70d1c76fd
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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