tert-Butyl carbazate → HCID 72490710, compound

HRID 968836Notes

Reaction equation

HRID 968836 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([F:19])[CH:18]=1)[CH:14]=O>C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]([CH:14]=[N:3][NH:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH:16]=[C:17]([F:19])[CH:18]=1

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 5881603,5-Difluorobenzaldehyde

Product 1

HCID 72490710HCID 72490710, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of t-butyl carbazate (4.99 g, 37.76 mmol) in ethyl acetate (10 mL) was added with stirring 3,5-difluorobenzaldehyde (5.50 g, 38.7 mmol) followed by hexanes (50 mL). Crystallization occurred and the resulting slurry was stirred at rt for 15 min, then cooled to 0° C. and held at that temperature for 45 min. The solids were filtered, rinsed with cold hexanes and dried in vacuo at 60° C. to afford the title compound as a solid (9.04 g, 93.3%): mp 196.4-196.8° C. (dec); 1H NMR (DMSO-d6) δ 11.16 (br s, 1 H), 7.96 (s, 1 H), 7.28 (m, 2 H), 7.21 (t, 1 H, J=2.2 Hz), 1.45 (s, 9 H); 13C NMR (DMSO-d6) δ 163.3 (dd, J=246.1, 13.5 Hz), 152.9, 141.2, 139.2 (t, J=9.6 Hz), 109.9 (dd, J=20.2, 5.8 Hz), 105.1 (t, J=25.9 Hz), 80.5, 28.7; IR (KBr mull) 3263, 2987, 1709, 1584, 1536 cm−1. A portion was recrystallized (ethyl acetate) for analysis. Anal. Calcd. for C12H14F2N2O2: C, 56.25; H, 5.51; F, 14.83; N, 10.93. Found: C, 56.11; H, 5.49; N, 10.86.

Workup

  1. customCrystallization
  2. temperaturecooled to 0° C.
  3. waitheld at that temperature for 45 min
  4. filtrationThe solids were filtered
  5. washrinsed with cold hexanes
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-e294f1111a82441e95d5b35b910be6e7
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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