Triethylamine → HCID 22594219, compound

HRID 1761014Notes

Reaction equation

HRID 1761014 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:17]=O)[C:12]([CH:15]=[O:16])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.[NH2:24][CH2:25][C:26]#[N:27].C(N(CC)CC)C>CN(C=O)C>[O:16]=[C:15]1[C:12]2[C:11](=[CH:10][C:9]([O:8][CH2:7][C:6]3[CH:19]=[CH:20][C:3]([C:2]([F:22])([F:21])[F:1])=[CH:4][CH:5]=3)=[CH:14][CH:13]=2)[CH2:17][N:27]1[CH2:26][C:25]#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 22594212HCID 22594212, compound

Product 1

HCID 22594219HCID 22594219, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 4-(4-trifluoromethyl-benzyloxy)-benzene-1,2-dicarbaldehyde (250.0 mg, 0.81 mmol) in DMF (7 mL) was added aminoacetonitrile HCl (150.1 mg, 1.62 mmol) and triethylamine (164.1 mg, 1.62 mmol) and the resulting mixture was warmed up to RT over 1 h and then heated at 50° C. for 1 h. After cooling to RT, the mixture was evaporated and the residue partioned between ethyl acetate and hydrochloric acid (1 N). The organic layer was then dried over sodium sulfate, filtered and evaporated to leave a clear oil which was purified by chromatography (SiO2, DCM:MeOH 9:1) to afford the title product (19.6 mg, 7%) as a light brown solid. MS m/e 345.2 (M−H−).

Workup

  1. temperatureheated at 50° C. for 1 h
  2. temperatureAfter cooling to RT
  3. customthe mixture was evaporated
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto leave a clear oil which
  8. customwas purified by chromatography (SiO2, DCM:MeOH 9:1)

Sources & evidence

ORD record
ord-d6b1f4b9f73e4d8a977a24fe9bba994b
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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