Diisopropylethylamine → N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydro-2H-pyran-4-carboxamide

HRID 1846494Notes

Reaction equation

HRID 1846494 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[CH2:27][CH2:26][CH:25]([C:28](Cl)=[O:29])[CH2:24][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:28]([CH:25]1[CH2:26][CH2:27][O:22][CH2:23][CH2:24]1)=[O:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2795505Oxane-4-carbonyl chloride2×HCID 669783384-Amino-3-chloro-5-nitrophenol

Product 1

HCID 66978264N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydro-2H-pyran-4-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 (2.54 mmol) DIPEA and 0.26 mL (2.54 mmol) tetrahydro-2H-pyran-4-carbonyl chloride were added and at RT the mixture was stirred for 2 h. A further 0.26 mL (2.54 mmol) tetrahydro-2H-pyran-4-carbonyl chloride were 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-4b4c88e1f7dd4b15bc6ddaa6045b0355
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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