Sodium Bicarbonate → HCID 21918692, compound

HRID 1356433Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[C:19](=[O:30])[CH2:18][S:17]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:16]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=3)[C:19](=[O:30])[CH2:18][S:17]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

1.3 g of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-3-(4-nitrophenyl)-4-thiazolidinone (3 mmol) and 3.4 g (15 mmol) of dihydrated tin chloride are dissolved in 25 ml of ethyl acetate. The reaction is maintained for 2 hours at 70° C. After the mixture has returned to ambient temperature, it is poured into a saturated solution of sodium hydrogen carbonate. The expected product is then extracted from the organic phase then it is washed 3 times with 10 ml of water. The 2-(3,5-di-t-butyl-4-hydroxyphenyl)-3-(4-aminophenyl)-4-thiazolidinone is purified on silica gel in an ethyl acetatelheptane mixture (1/1) and is obtained in the form of a beige oil with a yield of 69% (0.82 g).

Workup

customhas returned to ambient temperature
extractionThe expected product is then extracted from the organic phase
washit is washed 3 times with 10 ml of water
customThe 2-(3,5-di-t-butyl-4-hydroxyphenyl)-3-(4-aminophenyl)-4-thiazolidinone is purified on silica gel in an ethyl acetatelheptane mixture (1/1)
customis obtained in the form of a beige oil with a yield of 69% (0.82 g)

Sources & evidence

ORD record: ord-e768ebdf39494ea28df398eb044e7edc
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586454B2

Reaction notes

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