Oxalyl chloride → N,N-bis(2-methoxyethyl)-4-[3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-nitroaniline

HRID 1950863

Reaction equation

HRID 1950863 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][CH2:9][CH2:10][N:11]([CH2:24][CH2:25][O:26][CH3:27])[C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22].O[N:29]=[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39])[NH2:31].CCN(C(C)C)C(C)C>>[CH3:27][O:26][CH2:25][CH2:24][N:11]([CH2:10][CH2:9][O:8][CH3:7])[C:12]1[CH:20]=[CH:19][C:15]([C:16]2[O:18][N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])[N:29]=2)=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4652214N-Hydroxy-2-methoxy-benzamidineHCID 596065384-[Bis(2-methoxyethyl)amino]-3-nitrobenzoic acid

Product 1

HCID 25256655N,N-bis(2-methoxyethyl)-4-[3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-nitroaniline

Procedure

Oxalyl chloride (190 mg; 1.5 mmol; 3 eq.), Intermediate 31 (149 mg; 0.5 mmol; 1 eq.), Intermediate 1 (83 mg; 0.5 mmol, 1 eq.) and DIEA (194 mg; 1.5 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography (c-hexane/ethyl acetate, 50/50) followed by crystallisation from Et2O/n-pentane afforded the title compound as a yellow solid.

Workup

  1. customPurification by column chromatography (c-hexane/ethyl acetate, 50/50)
  2. customfollowed by crystallisation from Et2O/n-pentane

Sources & evidence

ORD record
ord-ba0ad6ea84d44d6ea25f84d87fa26d2e
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Linked notes

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