Water → (7-Iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

HRID 2308489Notes

Reaction equation

HRID 2308489 reaction equation
[CH3:1][O:2][C:3](=[O:16])[NH:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:8]=2[N:9]=1.C([O-])(=O)C.[Na+].[I:22]Cl.O>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:16])[NH:4][C:5]1[S:6][C:7]2[C:13]([I:22])=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:8]=2[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 21303403(4-Methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

Product 1

HCID 60117385(7-Iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(4-Methoxy-benzothiazol-2-yl)-carbamic acid methyl 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 l), 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 l), 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 l)
  5. filtrationfiltered off
  6. customdried at 60° C. for 12 hours

Sources & evidence

ORD record
ord-c11f3c56d1f944f091c8012fa5d42377
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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