Ethyl bromoacetate → HCID 20317766, compound

HRID 596970Notes

Reaction equation

HRID 596970 reaction equation
[Na].[NH:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[C:11](=[O:23])[C:12]4[C:17]([S:18](=[O:22])(=[O:21])[C:19]=3[CH:20]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:5][N:4]=[N:3]1.Br[CH2:25][C:26]([O:28]CC)=[O:27]>C(O)C>[C:26]([CH2:25][N:4]1[N:3]=[N:2][C:6]([C:7]2[CH:8]=[CH:9][C:10]3[C:11](=[O:23])[C:12]4[C:17]([S:18](=[O:21])(=[O:22])[C:19]=3[CH:20]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:5]1)([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545SodiumHCID 178515054HCID 178515054, compound

Product 1

HCID 20317766HCID 20317766, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.46 g) was dissolved in ethanol (20 ml) and 3-(5-tetrazolyl)thioxanthone-10,10-dioxide (6.24g) was added. Ethyl bromoacetate (3.34 g) was added to the mixture, which was boiled under reflux for 1.5 hr. The ester intermediate was deposited during this time, and after cooling was filtered off, washed with water and dried, m.p. 194°-195° C. The ester was boiled with concentrated hydrochloric acid (40 ml) and acetic acid (120 ml) for 2 hr. On cooling 3-(2-carboxymethyl-5-tetrazolyl)thioxanthone-10,10-dioxide crystallised out, and was filtered off, recrystallised from acetic acid, and dried, m.p. 252° C. with decomposition.

Workup

  1. temperatureunder reflux for 1.5 hr
  2. temperatureafter cooling
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried
  6. temperatureOn cooling 3-(2-carboxymethyl-5-tetrazolyl)thioxanthone-10,10-dioxide
  7. customcrystallised out
  8. filtrationwas filtered off
  9. customrecrystallised from acetic acid
  10. customdried

Sources & evidence

ORD record
ord-3c24c7a405d1462abf6d7b43a73c8bd0
Source dataset
uspto-grants-1977_03
Patent number
US04012499

Reaction notes

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