1,1'-Carbonyldiimidazole → HCID 131718079, compound

HRID 274474Notes

Reaction equation

HRID 274474 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:13][C:14]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=1[O:26][CH3:27].[NH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36](=[O:42])[NH:37][C:38]([CH3:41])([CH3:40])[CH3:39]>O1CCCC1>[OH:13][C:14]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:17]([C:18]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36](=[O:42])[NH:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:20])=[CH:16][C:15]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 155279394-Hydroxy-3-methoxy-5-nitrobenzoic acidHCID 21459094HCID 21459094, compound

Product 1

HCID 131718079HCID 131718079, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.9 g of 1,1'-carbonyldiimidazole are added to a solution of 10.7 g of 4-hydroxy-3-methoxy-5-nitrobenzoic acid in 500 ml of dry tetrahydrofuran and the reaction mixture is subsequently heated to 65°-70° for 5 hours. It is then cooled to room temperature and a solution of 21.6 g of 6-aminohexyl-t-butylcarbamate in 50 ml of dry tetrahydrofuran is added dropwise thereto within 15 minutes. The reaction mixture is then heated to 65°-70° for 18 hours, evaporated, the residue is suspended in ethyl acetate, suction filtered and the suction filtered material is chromatographed on silica gel with acetone/methylene chloride (3:1). There is obtained [6-(4-hydroxy-5-nitro-m-anisamido)hexyl]-t-butylcarbamate of m.p. 145°-147° (from isopropanol).

Workup

  1. temperaturethe reaction mixture is subsequently heated to 65°-70° for 5 hours
  2. temperatureThe reaction mixture is then heated to 65°-70° for 18 hours
  3. customevaporated
  4. filtrationsuction filtered
  5. filtrationthe suction filtered material
  6. customis chromatographed on silica gel with acetone/methylene chloride (3:1)

Sources & evidence

ORD record
ord-e82e28bf0ddc44bb807015d2cd7e4f54
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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