3-Aminobenzoic Acid → 3-Azidobenzoic Acid

HRID 2109177Notes

Reaction equation

HRID 2109177 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3].NC1C(OC)=C(NS(C)(=O)=O)C=C(C(C)(C)C)C=1.[N:31]([C:34]1[CH:35]=[C:36]([CH:57]=[CH:58][C:59]=1C)[C:37]([NH:39][C:40]1[CH:45]=[C:44]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:43]=[C:42]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[C:41]=1[O:55][CH3:56])=[O:38])=[N+:32]=[N-:33].NC1C=C(C=CC=1)C(O)=O.N(C1C=C(C=CC=1C)C(O)=O)=[N+]=[N-]>>[N:31]([C:34]1[CH:35]=[C:36]([CH:57]=[CH:58][CH:59]=1)[C:37]([NH:39][C:40]1[CH:45]=[C:44]([C:46]([CH3:47])([CH3:48])[CH3:49])[CH:43]=[C:42]([NH:50][S:51]([CH3:54])(=[O:52])=[O:53])[C:41]=1[O:55][CH3:56])=[O:38])=[N+:32]=[N-:33].[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3]

Participants

7

Reactant 5

HCID 74193-Aminobenzoic AcidHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 110737433-Azidobenzoic AcidHCID 179730913-Azido-4-methylbenzoic acidHCID 210792023-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide

Product 2

HCID 110737433-Azidobenzoic AcidHCID 21097303HCID 21097303, compound

Procedure

3-Azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-benzamide was prepared from 3-azido benzoic acid and N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methane-sulfonamide in the same manner as 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide (Example 15). 3-Azido benzoic acid was prepared from 3-amino benzoic acid in the same manner as 3-azido-4-methyl benzoic acid.

Sources & evidence

ORD record
ord-85dd8a042a4041259eac3c21767dcaa9
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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