Trichloroacetyl isocyanate → 7-Benzyloxy-2-ethylthiazolo[4,5-c]quinolin-4-amine

HRID 913358Notes

Reaction equation

HRID 913358 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:22][C:21]([CH2:23][CH3:24])=[N:20][C:14]=3[CH:15]=[N+:16]([O-])[C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:29]=C=O)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:22][C:21]([CH2:23][CH3:24])=[N:20][C:14]=3[C:15]([NH2:29])=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 673930907-Benzyloxy-2-ethylthiazolo[4,5-c]quinoline 5-oxide

Product 1

HCID 589650297-Benzyloxy-2-ethylthiazolo[4,5-c]quinolin-4-amineYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred pale orange solution of 7-benzyloxy-2-ethylthiazolo[4,5-c]quinoline 5-oxide (15.00 g, 44.6 mmol) in dichloromethane (200 mL), at room temperature, was slowly added trichloroacetylisocyanate (1.05 eq., 5.6 ml 46.8 mmol). The solution was maintained at room temperature for 18 hours. At this time the reaction was quenched by the addition of concentrated ammonium hydroxide solution (60 ml). An off-white precipitate formed and was collected by vacuum filtration. Recrystallization from acetonitrile provided 11.3 g of 7-benzyloxy-2-ethylthiazolo[4,5-c]quinolin-4-amine as a white crystalline solid, mp 208-209° C. MS (APCI) m/z 336.1 (M+H)+; Anal. calcd for C19H17N3OS: C, 68.03; H, 5.11; N, 12.53. Found: C, 67.45; H, 4.83; N, 12.41.

Workup

  1. customat room temperature
  2. customAt this time the reaction was quenched by the addition of concentrated ammonium hydroxide solution (60 ml)
  3. customAn off-white precipitate formed
  4. filtrationwas collected by vacuum filtration
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-4bdc6ca2cce84d188e98acf77f584c91
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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