Tetrahydrofuran → HCID 824395, compound

HRID 1045380Notes

Reaction equation

HRID 1045380 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CCN(C(C)C)C(C)C.CN(C(O[N:28]1[N:36]=N[C:30]2C=CC=C[C:29]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C[O:45]CC1>>[C:29]([NH:28][NH:36][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=1)(=[O:45])[CH3:30]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 120603-Iodobenzoic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 824395HCID 824395, compound

Procedure

To a suspension of 3-iodobenzoic acid (2.0 g, 8.06 mmol) in 60 ml of THF there are added, in succession, DIPEA (1.83 ml, 10.48 mmol) and TBTU (2.59 g, 8.06 mmol). The reaction mixture is stirred overnight at ambient temperature. 1.19 g (16.12 mmol) of acetyl hydrazide are added and the reaction mixture is heated at reflux for 30 hours. After evaporation to dryness, the residue is taken up in water with a small amount of CH2Cl2; a thick precipitate forms, which is filtered off to yield the expected product.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 30 hours
  3. customAfter evaporation to dryness
  4. filtrationa thick precipitate forms, which is filtered off

Sources & evidence

ORD record
ord-30e15cc75a064ee5bba6b0e58eec69b0
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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