Dicyclohexylcarbodiimide → HCID 85720097, compound

HRID 1977348Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:5](N(OC)C)=[O:6].NC1C=C(C=C([N+]([O-])=O)C=1)C(O)=O.[F:30][C:31]1[C:36]([OH:37])=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41].C1CCC(N=C=NC2CCCCC2)CC1>>[F:30][C:31]1[C:32]([F:41])=[C:33]([F:40])[C:34]([F:39])=[C:35]([F:38])[C:36]=1[O:37][C:5](=[O:6])[C:4]1[CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:2]([NH2:1])[CH:3]=1

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 13041Pentafluorophenol

HCID 2393423-Amino-5-nitrobenzoic acid

HCID 18617192HCID 18617192, compound

Product 1

HCID 85720097HCID 85720097, compound

Procedure

Starting material (1(b)) was prepared as follows. A mixture of 3-amino-5-nitrobenzoic acid (10 g), pentafluoro-phenol (10 g) and DCCI (11.3 g) was stirred at ambient temperature for 24 hours. The reaction mixture was filtered and the filtrate poured onto a chromatography column which was then eluted with ethyl acetate/hexane (10:90) to give 3-amino-5-nitrobenzoic acid 2,3,4,5,6-pentafluorophenyl ester (1(a)) as a yellow solid (5.8 g).

Workup

customwas prepared
filtrationThe reaction mixture was filtered
additionthe filtrate poured onto a chromatography column which
washwas then eluted with ethyl acetate/hexane (10:90)

Sources & evidence

ORD record: ord-d1222f987e074e4ca23009202051a8cc
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232338B1

Reaction notes

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