Hydrochloric Acid → HCID 15053522, compound

HRID 2107268Notes

Reaction equation

HRID 2107268 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[NH:12][C:13]2[S:14][CH:15]=[C:16]([C:18](=[O:24])[C:19](OCC)=[O:20])[N:17]=2)=[CH:6][CH:5]=1.CO.Cl>O1CCCC1.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[NH:12][C:13]2[S:14][CH:15]=[C:16]([CH:18]([OH:24])[CH2:19][OH:20])[N:17]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 15053495HCID 15053495, compound

Product 1

HCID 15053522HCID 15053522, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.4 g of sodium borohydride were added to a suspension of 5 g of ethyl 2-(3-p-bromophenylureido)thiazol-4-ylglyoxylate in 60 ml of tetrahydrofuran, then 20 ml of methanol were added dropwise over a period of 1 hour while heating the reaction mixture under reflux, and the reaction mixture was thereafter heated under reflux for a further 1 hour. The reaction mixture was poured into water and neutralized with 3N hydrochloric acid. The crystals which precipitated out were collected by filtration, washed with water and dried, giving crude 1-[2-(3-p-bromophenyl- ureido)thiazol-4-yl]ethane-1,2-diol.

Workup

  1. temperaturewhile heating the reaction mixture
  2. temperatureunder reflux
  3. temperaturethe reaction mixture was thereafter heated
  4. temperatureunder reflux for a further 1 hour
  5. customThe crystals which precipitated out
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f864adfd65934621b21548f0452048d7
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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