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Diisopropylethylamine → N-(4-(benzyloxy)-2-methyl-6-nitrophenyl)tetrahydro-2H-pyran-4-carboxamide

HRID 1846503
Notes
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Reaction equation

HRID 1846503 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:12]([NH2:13])=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[O:29]1[CH2:34][CH2:33][CH:32]([C:35](Cl)=[O:36])[CH2:31][CH2:30]1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:12]([NH:13][C:35]([CH:32]2[CH2:33][CH2:34][O:29][CH2:30][CH2:31]2)=[O:36])=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2795505Oxane-4-carbonyl chloride2×HCID 669780234-(Benzyloxy)-2-methyl-6-nitroaniline

Product 1

HCID 66978329N-(4-(benzyloxy)-2-methyl-6-nitrophenyl)tetrahydro-2H-pyran-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.22 g (0.85 mmol) 4-(benzyloxy)-2-methyl-6-nitroaniline were placed in 5 mL DCM. 0.17 mL (1.00 mmol) DIPEA and 0.10 mL (1.00 mmol) tetrahydro-2H-pyran-4-carbonyl chloride were added and the mixture was stirred for 2 h at RT. A further 0.10 mL (1.00 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-9f8559e9917d4f86a7802a1127fed117
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952014B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes