Water → HCID 21865042, compound

HRID 1060292Notes

Reaction equation

HRID 1060292 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:15])[OH:14])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].[I:21]Cl.O>C(O)(=O)C>[I:21][C:6]1[C:7]2[S:11][C:10]([NH:12][C:13](=[O:14])[OH:15])=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 21865187HCID 21865187, compound

Product 1

HCID 21865042HCID 21865042, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(4-Methoxy-benzothiazol-2-yl)-carbamic acid methyll ester (31.0 g, 130 mmol) and sodium acetate (32.3 g, 394 mmol) are dissolved in 400 ml of glacial acetic acid and slowly treated with iodine monochloride (13.5 ml, 264 mmol) at 0° C. The reaction mixture is then slowly warmed to room temperature and stirred for 15 hours. After addition of water (1.3 1), the formed precipitate is filtered off and washed with water. The filter cake is then dissolved in a minimal amount of tetrahydrofurane (about 150 ml) and decolorized with 1M aqueous sodium thiosulfate. The product is precipitated by the addition of water (about 2.0 1), filtered off and dried at 60° C. for 12 hours. 42.3 g (89%) white solid. MS: m/e=364 (M+).

Workup

  1. filtrationthe formed precipitate is filtered off
  2. washwashed with water
  3. dissolutionThe filter cake is then dissolved in a minimal amount of tetrahydrofurane (about 150 ml)
  4. customThe product is precipitated by the addition of water (about 2.0 1)
  5. filtrationfiltered off
  6. customdried at 60° C. for 12 hours

Sources & evidence

ORD record
ord-16e50209cd8446c6806ba6a57cb6ed4a
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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