Acetic Acid → HCID 68712508, compound

HRID 1820131Notes

Reaction equation

HRID 1820131 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([N+:26]([O-])=O)=[C:21]([CH3:29])[CH:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.[Zn]>[C:1]([O:5][C:6](=[O:30])[N:7]([C:19]1[CH:20]=[C:21]([CH3:29])[C:22]([NH2:26])=[C:23]([CH3:25])[CH:24]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 68710411HCID 68710411, compound

Product 1

HCID 68712508HCID 68712508, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To (3,5-Dimethyl-4-nitro-phenyl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (9.5 g) in ethanol (150 mL) was added zinc dust (22 g) and acetic acid (13 mL). The reaction mixture was stirred 3 hours and then filtered. The solution was concentrated in vacuo, redissolved in ethyl acetate (100 mL) and extracted with water (2×50 mL). The organic phase was dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an off white compound. Yield. 6.5 g (78%). LC-MS (m/z) 395 (MH+); tR=3.06, (UV, ELSD) 89%, 96%. 1H NMR (500 MHz, CDCl3): 1.40 (s, 9H), 2.10 (s, 6H), 3.50 (broad, 2H), 4.75 (s, 2H), 6.70 (s, 2H), 7.35 (d, 2H), 7.55 (d, 2H).

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionredissolved in ethyl acetate (100 mL)
  4. extractionextracted with water (2×50 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2289eeedc5114e9aacde00dc2ac74e22
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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