tert-Butoxy bis(dimethylamino)methane → HCID 53750001, compound

HRID 1708533Notes

Reaction equation

HRID 1708533 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Cl:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(O[CH:18](N(C)C)[N:19]([CH3:21])[CH3:20])(C)(C)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:18][N:19]([CH3:21])[CH3:20])[C:5]([Cl:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 2516781,4-dichloro-2-methyl-5-nitrobenzene

Product 1

HCID 53750001HCID 53750001, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Dichloro-4-methyl-nitrobenzene (50 g, 0.24 mol) was heated at reflux, in tetrahydrofuran (200 ml), with t-butoxy-bis(dimethylamino)methane (63.3 g, 0.364 mol) for 8 hours. The reaction mixture was cooled to room temperature and slowly poured into hexanes (3L) with stirring. The desired product was collected by filtration as a dark red solid, 36.9 g, 58% yield. mp 173°-5° C. NMR (CDCl3) δ 8.01 (s, 1), 7.32 (s, 1), 7.08 (d, 1), 5.27 (d, 1), 3.00 (s, 6). Analysis Calculated for C10H10N2O2Cl2 : C, 45.99; H, 3.86; N, 10.73, Found: C, 45.91; H, 3.72; N, 10.61.

Workup

  1. filtrationThe desired product was collected by filtration as a dark red solid, 36.9 g, 58% yield

Sources & evidence

ORD record
ord-905973fa2921471b9ab160931228501e
Source dataset
uspto-grants-1994_10
Patent number
US05359068

Reaction notes

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