Sodium Hydroxide → HCID 20317764, compound

HRID 596967Notes

Reaction equation

HRID 596967 reaction equation
Br[CH2:2][CH2:3][C:4]([O:6]CC)=[O:5].[NH:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[C:18](=[O:30])[C:19]4[C:24]([S:25](=[O:29])(=[O:28])[C:26]=3[CH:27]=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:12][N:11]=[N:10]1.[OH-].[Na+]>CC(C)=O.O>[C:4]([CH2:3][CH2:2][N:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[C:18](=[O:30])[C:19]4[C:24]([S:25](=[O:28])(=[O:29])[C:26]=3[CH:27]=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:12][N:11]=[N:10]1)([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 68320Ethyl 3-bromopropionateHCID 178515054HCID 178515054, compound

Product 1

HCID 20317764HCID 20317764, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Ethyl 3-bromopropionate (9.05 g) in acetone (70 ml) was added to 3-(5-tetrazolyl)thioxanthone-10,10-dioxide (15.6 g) and sodium hydroxide (2.0 g) in water (15 ml). The mixture was boiled under reflux for 8 hr. On cooling the ester product crystallised out and was filtered off, washed with dilute sodium bicarbonate solution, and recrystallised from ethanol, m.p. 143°-145° C. The ester (4.5 g) was boiled with a mixture of concentrated hydrochloric acid (40 ml) and acetic acid (120 ml) for 3 hr. On cooling, 3-((2-carboxyethyl)-5-tetrazolyl)thioxanthone-10,10-dioxide crystallised out and was filtered off and washed with water, m.p. 206°-207° C. Found: C, 53.10%; H, 3.22%; N, 14.59%. C17H12N4O5S requires C, 53.12%; H, 3.15%; N, 14.58%.

Workup

  1. temperatureunder reflux for 8 hr
  2. customcrystallised out
  3. filtrationwas filtered off
  4. washwashed with dilute sodium bicarbonate solution
  5. customrecrystallised from ethanol, m.p. 143°-145° C
  6. additionThe ester (4.5 g) was boiled with a mixture of concentrated hydrochloric acid (40 ml) and acetic acid (120 ml) for 3 hr
  7. temperatureOn cooling
  8. custom3-((2-carboxyethyl)-5-tetrazolyl)thioxanthone-10,10-dioxide crystallised out
  9. filtrationwas filtered off
  10. washwashed with water, m.p. 206°-207° C

Sources & evidence

ORD record
ord-39acdf171db54783a65ef48643263e46
Source dataset
uspto-grants-1977_03
Patent number
US04012499

Reaction notes

Loading…