HCID 22283070, compound → HCID 22283236, compound

HRID 1060298Notes

Reaction equation

HRID 1060298 reaction equation
[Br:1][CH:2]([CH3:20])[CH:3]([C:5]1[C:13]2[S:12][C:11]([NH:14][C:15](=[O:17])[OH:16])=[N:10][C:9]=2[C:8]([O:18][CH3:19])=[CH:7][CH:6]=1)[OH:4]>O.C(O)(=O)C>[Br:1][CH:2]([CH3:20])[C:3]([C:5]1[C:13]2[S:12][C:11]([NH:14][C:15](=[O:16])[OH:17])=[N:10][C:9]=2[C:8]([O:18][CH3:19])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 22283070HCID 22283070, compound

Product 1

HCID 22283236HCID 22283236, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

5.0 g of [7-(2-bromo-1-hydroxy-propyl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyll ester 0.0133 Mol) were suspended in water (30 ml) and 2.0 g of CrO3 (0.02 Mol), dissolved in acetic acid (30 ml), were added. The reaction mixture was heated to 70° C. for 2 hrs. and then evaporated to dryness. The residue was taken up in sat. NaHCO3 (200 ml), extracted 4× with ethyl acetate (200 ml each) and the combined organic phases were dried over MgSO4. The title compound was obtained as orange crystals (74%); F.p.: 199-201° C.

Workup

  1. additionwere added
  2. customand then evaporated to dryness
  3. extractionextracted 4× with ethyl acetate (200 ml each)
  4. dry with materialthe combined organic phases were dried over MgSO4

Sources & evidence

ORD record
ord-218f6e8c368143c59e4e05c5a67d2bfe
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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