Propionic Acid → 3-{Ethyl-[3-methyl-4-(5-nitro-thiazol-2-ylazo)-phenyl]-amino}-propionic acid vinyl ester

HRID 252892

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.C(O)(=O)CC.N(OS(=O)(=O)O)=O.[CH:22]([O:24][C:25](=[O:38])[CH2:26][CH2:27][N:28]([CH2:36][CH3:37])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=1)=[CH2:23].S(=O)(=O)(O)[NH2:40]>CO.C(O)(=O)C>[CH:22]([O:24][C:25](=[O:38])[CH2:26][CH2:27][N:28]([CH2:36][CH3:37])[C:29]1[CH:34]=[CH:33][C:32]([N:40]=[N:1][C:2]2[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=2)=[C:31]([CH3:35])[CH:30]=1)=[CH2:23]

Participants

Conditions

Temperature: 5 °C

Procedure

4.4 parts of 2-amino-5-nitrothiazole, 20 parts of propionic acid and 30 parts of acetic acid were charged and cooled to 5° C. 11.4 parts of 40% (w/w) nitrosyl sulfuric acid were added, whilst the temperature was held below 10° C. The diazotization mixture was stirred for a further 2 hrs at 5-10° C. To a separate vessel were charged 7.0 parts of 3-(ethyl-[3-methylphenyl]-amino)-propionic acid vinyl ester, 100 parts of methanol, 1 part sulfamic acid and 100 parts of ice. With stirring, the diazotization mixture was slowly added followed by a further 300 parts of ice. The reaction mixture was stirred over night and the product was isolated by filtration, washed subsequently with water, methanol and again water, then dried to yield 9.5 parts of 3-{ethyl-[3-methyl-4-(5-nitro-thiazol-2-ylazo)-phenyl]-amino}-propionic acid vinyl ester. λmax=602 nm (DMF).

Workup

customwas held below 10° C
stirringWith stirring
additionthe diazotization mixture was slowly added
stirringThe reaction mixture was stirred over night
customthe product was isolated by filtration
washwashed subsequently with water, methanol and again water
customdried

Sources & evidence

ORD record: ord-35a24bb26dbf4fc9a03ad3f5057ed95c
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871446B2

Linked notes

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