Triethylamine → HCID 18784610, compound

HRID 1108253Notes

Reaction equation

HRID 1108253 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:13]([N:19]=[C:20]=[S:21])[CH:14]1[O:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(O)C>[I:12][C:8]1[CH:7]=[C:3]2[C:2](=[C:10]([I:11])[CH:9]=1)[NH:1][C:20](=[S:21])[N:19]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][O:18]1)[C:4]2=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69116Benzoic acid, 2-amino-3,5-diiodo-HCID 1421082-(Isothiocyanatomethyl)oxolane

Product 1

HCID 18784610HCID 18784610, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3,5-diiodobenzoic acid (1.09 g, 2.57 mmol), tetrahydrofurfuryl isothiocyanate (0.35 g, 2.43 mmol) and triethylamine (0.26 g, 2.57 mmol) in 3.5 mL of ethanol was heated to reflux for about 6 h, and then was allowed to cool to room temperature. The ensuing precipitate was filtered and washed with ethanol (1×20 mL), hexanes (1×mL), and then dried to deliver 0.86 g of the title compound of Step A. 1H NMR (400 MHz, Me2SO-d6): δ 1.64-1.75 (m,1H), 1.75-1.85 (m,1H), 1.86-2.0 (m,2H), 3.57-3.65 (m,1H), 3.70-3.81 (m,1H), 4.26-4.34 (m,1H), 4.36-4.44 (m,1H), 4.52-4.60 (m,1H), 8.19 (d,1H), 8.56 (d,1H), 10.1 (br s,1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 6 h
  3. filtrationThe ensuing precipitate was filtered
  4. washwashed with ethanol (1×20 mL), hexanes (1×mL)
  5. customdried

Sources & evidence

ORD record
ord-66f6af78b9d347c1a41f763f992213ec
Source dataset
uspto-grants-2000_05
Patent number
US06066638

Reaction notes

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