Water → HCID 23577002, compound

HRID 350618Notes

Reaction equation

HRID 350618 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[NH2:14])([CH3:4])([CH3:3])[CH3:2].Cl[C:16](=[O:21])[C:17]([O:19][CH3:20])=[O:18].CCN(CC)CC.O>C(Cl)Cl>[CH3:20][O:19][C:17](=[O:18])[C:16]([NH:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 8261032-Tert-butyl-5-nitroaniline

Product 1

HCID 23577002HCID 23577002, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-tert-Butyl-5-nitro-phenylamine (4.04 g, 20.80 mmol) in CH2Cl2 (20 mL) at 0° C. was added 1.1 equiv of Methyl chlorooxoacetate (2.10 mL, 22.88 mmol) and followed by dropwise addition of 1.1 equiv of Et3N (3.19 mL, 22.88 mmol). After stirring at 0° C. and allowing to warm up to room temperature over 4 hrs, the reaction mixture was treated with water (20 mL), stirred for 10 min and then partitioned between EtOAc/water. The organic phase was washed with 0.5N HCl (2×25 mL), and saturated NaCl solution (50 mL), dried over Na2SO4 and evaporated to dryness. The residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (5–25%) to give the title compound (3.25 g, 56%) as light yellow crystals. TLC (30% EtOAc/Hexane) Rf=0.39; 1HNMR (CDCl3) δ 9.36 (br.s, 1H), 8.97 (d, J=2.4 Hz, 1H), 8.02 (dd, J=9.0, 2.4 Hz, 1H), 7.60 (d, J=9.0 Hz, 1H), 4.03 (s, 3H), 1.52 (s, 9H).

Workup

  1. temperatureto warm up to room temperature over 4 hrs
  2. stirringstirred for 10 min
  3. custompartitioned between EtOAc/water
  4. washThe organic phase was washed with 0.5N HCl (2×25 mL), and saturated NaCl solution (50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (5–25%)

Sources & evidence

ORD record
ord-0b3db87c421e452d9d4527b81cb1380a
Source dataset
uspto-grants-2007_02
Patent number
US07183260B2

Reaction notes

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