Diisopropylethylamine → N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydrofuran-3-carboxamide

HRID 1846490

Reaction equation

HRID 1846490 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[CH:4][C:3]=1[Cl:12].CCN(C(C)C)C(C)C.[O:22]1[CH2:26][CH2:25][CH:24]([C:27](Cl)=[O:28])[CH2:23]1>C(Cl)Cl>[Cl:12][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:1][C:27]([CH:24]1[CH2:25][CH2:26][O:22][CH2:23]1)=[O:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 14020412Tetrahydrofuran-3-carbonyl chloride2×HCID 669783384-Amino-3-chloro-5-nitrophenol

Product 1

HCID 66978219N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydrofuran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.40 g (2.12 mmol) 4-amino-3-chloro-5-nitrophenol were placed in 5 mL DCM. 0.44 mL DIPEA and 0.34 g tetrahydrofuran-3-carbonyl chloride were added and the mixture was stirred for 2 h at RT. A further 0.34 g tetrahydrofuran-3-carbonyl chloride was added and the mixture was stirred overnight at RT. The reaction mixture was diluted with DCM and washed with water. The organic phase was evaporated down i.vac.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. washwashed with water
  3. customThe organic phase was evaporated down i.vac

Sources & evidence

ORD record
ord-750612a2b2be49fea853381032bdd2ab
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Linked notes

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