Triethylamine → HCID 4444271, compound

HRID 1066877Notes

Reaction equation

HRID 1066877 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:18]=[C:19]=[S:20])[CH:13]1[O:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(O)C>[Br:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:19](=[S:20])[N:18]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][O:17]1)[C:4]2=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 798582-Amino-5-bromobenzoic acidHCID 1421082-(Isothiocyanatomethyl)oxolane

Product 1

HCID 4444271HCID 4444271, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-bromobenzoic acid (8.0 g, 37.0 mmol), tetrahydrofurfuryl isothiocyanate (5.0 g, 34.9 mmol) and triethylamine (5.0 mL, 3.6 g, 35.6 mmol) in ethanol (48 mL) was heated at reflux for 2 h. The reaction mixture was then allowed to cool to room temperature and filtered. The resulting filter cake was washed with 50 mL of cold ethanol, followed by 50 mL of hexanes to provide 10.8 g of the title compound of Step A as a solid melting at 230-232° C. 1H NMR (400 MHz, Me2SO-d6): δ 1.63-2.0 (m,4H), 3.58-3.68 (m,1H), 3.74-3.82 (m,1H), 4.32 (dd,1H), 4.39-4.50 (m,1H), 4.58 (dd,1H), 7.37 (d,1H), 7.91 (d,1H), 8.02 (s,1H), 13.1 (br s,1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. filtrationThe resulting filter cake
  5. washwas washed with 50 mL of cold ethanol

Sources & evidence

ORD record
ord-d76630f41cc54cc8a598d8c3f572cf35
Source dataset
uspto-grants-2001_06
Patent number
US06245770B1

Reaction notes

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