Acetic Acid → HCID 178476599, compound

HRID 1370105Notes

Reaction equation

HRID 1370105 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[N+:17]([O-:19])=[O:18])[CH2:4][CH2:3]1.[C:20](O)(=[O:22])[CH3:21].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:20]([O:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[N+:17]([O-:19])=[O:18])[CH2:4][CH2:3]1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178510062HCID 178510062, compound

Product 1

HCID 178476599HCID 178476599, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(trans-4-hydroxycyclohexylamino)-3-nitrobenzonitrile (1.0 g), acetic acid (345 mg) and diethyl azodicarboxylate (2.17 g, 40% solution in toluene) in anhydrous tetrahydrofuran (25 mL) was added portionwise triphenylphosphine (1.31 g) at 0° C., and the mixture was stirred at ambient temperature for 2 hours. The mixture was evaporated in vacuo and the residue was subjected to a silica gel column chromatography eluting with a mixture of n-hexane and ethyl acetate (5:1 to 3:1) and then chloroform. The obtained substance was triturated with methanol to give 4-(cis-4-acetoxycyclohexylamino)-3-nitrobenzonitrile (530 mg) as yellow powders.

Workup

  1. customThe mixture was evaporated in vacuo
  2. washeluting with a mixture of n-hexane and ethyl acetate (5:1 to 3:1)
  3. customThe obtained substance was triturated with methanol

Sources & evidence

ORD record
ord-f41c58b5cc264e66b6a69d8eacb7c29c
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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