Formic Acid → HCID 178513487, compound

HRID 1592936Notes

Reaction equation

HRID 1592936 reaction equation
C(O[C:4]([C:6]1[C:10]([C:11]([O:13]CC)=O)=[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[O:8][C:7]=1[NH2:25])=[O:5])C.C[N:27]([CH:29]=O)C.C(O)=O.C([NH2:36])=O>O>[OH:5][C:4]1[C:6]2[C:10]([C:11]([NH2:36])=[O:13])=[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=3)[O:8][C:7]=2[N:25]=[CH:29][N:27]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 713FormamideHCID 6228DimethylformamideHCID 69414008HCID 69414008, compound

Product 1

HCID 178513487HCID 178513487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

72.9 g of 2-amino-5-(3-nitrophenyl)furan-3,4-dicarboxylic acid diethyl ester are stirred for ca. 23 h at 140° C. under N2 in 200 ml of formamide, 100 ml of DMF and 40 ml of 98-100% formic acid. After cooling the solution, the reaction mixture is diluted with H2O, left to stand for 8 h and filtered by suction. The residue is dried in a HV, boiled in 300 ml of acetonitrile, filtered by suction, washed with ice-cold acetonitrile and dried in a HV. This second residue is boiled in 200 ml of methylene chloride, filtered by suction whilst warm, washed with methylene chloride and dried in a HV. The residue obtained contains the product; m.p.: 212-220° C. IR: 3528w, 3246m, 3092m, 2985w, 1936w, 1721s, 1589m, 1543s, 1482m, 1429w, 1378s, 1352s, 1323m, 1287m, 1234m, 1196m, 1076m, 1042s. In the product thus obtained, 4-hydroxy-6-(3-nitrophenyl)furo[2,3-d]pyrimidin-5-carboxylic acid amide is obtained as a by-product. This is obtained in analysis-pure form by recrystallisation from DMF; m.p.: ca. 380° C. (decomposition) IR: 3338m, 3180-2810w (multiplett), 1708s, 1676s, 1589w, 1560m, 1526s, 1406w, 1348s, 1220w, 1105w, 1081w, 1041w, 920w, 899w, 880w, 803w, 740w, 676w.

Workup

  1. temperatureAfter cooling the solution
  2. waitleft
  3. filtrationfiltered by suction
  4. customThe residue is dried in a HV
  5. filtrationfiltered by suction
  6. washwashed with ice-cold acetonitrile
  7. customdried in a HV
  8. filtrationfiltered by suction
  9. temperaturewhilst warm
  10. washwashed with methylene chloride
  11. customdried in a HV
  12. customThe residue obtained
  13. customIn the product thus obtained

Sources & evidence

ORD record
ord-68cb73733e0740b3ba95d8ac98d585b3
Source dataset
uspto-grants-2007_11
Patent number
US07294633B2

Reaction notes

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