1,2-Ethanediamine, N1,N1,N2-trimethyl- → N,N,N'-Trimethyl-N'-(5-nitro-benzooxazol-2-yl)-ethane-1,2-diamine

HRID 601549Notes

Reaction equation

HRID 601549 reaction equation
CS[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=2[N:7]=1.[CH3:15][N:16]([CH3:21])[CH2:17][CH2:18][NH:19][CH3:20]>>[CH3:15][N:16]([CH3:21])[CH2:17][CH2:18][N:19]([CH3:20])[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 152521182-(Methylthio)-5-nitrobenzo[d]oxazole

Product 1

HCID 57501782N,N,N'-Trimethyl-N'-(5-nitro-benzooxazol-2-yl)-ethane-1,2-diamineYield 44.5%

Procedure

Prepare the title compound by essentially following the procedure as described in Preparation 139, using 2-methylsulfanyl-5-nitro-benzooxazole (5.0 g, 23.8 mmol) and N,N,N′-Trimethyl-ethane-1,2-diamine (15.4 mL, 118.9 mmol) at 140° C. The product is purified by silica gel flash column chromatography (330 g column, eluting with 5% 2N NH3 in MeOH/CH2Cl2) to yield the desired product (2.8 g, 44%). MS (ES+) 265.3 (M+1)+.

Workup

  1. customas described in Preparation 139
  2. customat 140° C
  3. customThe product is purified by silica gel flash column chromatography (330 g column, eluting with 5% 2N NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-688f44e68b1044e2b86c4ba149efaa58
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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