1,2-Ethanediamine, N1,N1,N2-trimethyl- → Bis-benzyloxy benzoic acid

HRID 76091Notes

Reaction equation

HRID 76091 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CNCCN(C)C>>[CH2:11]([O:10][C:6]1[C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:26])=[O:2])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 10665397Methyl 2,3-bis(benzyloxy)benzoate

Product 1

HCID 10520703Bis-benzyloxy benzoic acid

Procedure

In another embodiment the compounds can be prepared as shown in Scheme IV. A bromo-nitrobenzene (1) can be reacted with N1,N2,N2-trimethylethane-1,2-diamine to give N1-(nitrophenyl)-N1,N2, N2-trimethylethane-1,2-diamine (2). A solution of (2) in can be subjected to hydrogenation, passed through a short pad of celite, washed with MeOH and evaporated under reduced pressure. Thiocarbodiimidazole can then be added to (2) to give the N1-(isothiocyanato-phenyl)-)-N1,N2,N2-trimethylethane-1,2-diamine (3).

Workup

  1. customIn another embodiment the compounds can be prepared

Sources & evidence

ORD record
ord-3d3d43bde741434782933f206dc1ee08
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Reaction notes

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