Water → 4-(Cyclopropylmethyl-amino)-benzenesulfonic acid 4-amino-3-nitro-phenyl ester

HRID 1823780Notes

Reaction equation

HRID 1823780 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[CH:22]1([CH2:25][NH2:26])[CH2:24][CH2:23]1.O>CN1CCCC1=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:26][CH2:25][CH:22]3[CH2:24][CH2:23]3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 75646CyclopropanemethanamineHCID 120188434-Amino-3-nitrophenyl 4-fluorobenzenesulfonate

Product 1

HCID 865960784-(Cyclopropylmethyl-amino)-benzenesulfonic acid 4-amino-3-nitro-phenyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-fluoro-benzenesulfonic acid 4-amino-3-nitro-phenyl ester (800 mg) and cyclopropylmethylamine (890 μl) in N-methylpyrrolidinone (8 ml) was heated at 110° C. in a sealed tube for 14 hours. The reaction mixture was then poured into water (150 ml) and extracted three times with ethyl acetate (40 ml). The combined extracts were dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (50:50, v/v) to give 4-(cyclopropylmethyl-amino)-benzenesulfonic acid 4-amino-3-nitro-phenyl ester (786 mg) as a yellow solid.

Workup

  1. extractionextracted three times with ethyl acetate (40 ml)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (50:50

Sources & evidence

ORD record
ord-2d1b2fa666854d8285f5d226918de8ec
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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