Hydrochloric Acid → (4-Methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

HRID 51855

Reaction equation

HRID 51855 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1.N1C=CC=CC=1.Cl[C:20]([O:22][CH3:23])=[O:21].Cl>ClCCl>[CH3:23][O:22][C:20](=[O:21])[NH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 216224-Methoxy-2-aminobenzothiazole

Product 1

HCID 21303403(4-Methoxy-benzothiazol-2-yl)-carbamic acid methyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 23.6 g (131 mmol) 2-amino-4-methoxybenzothiazole and 12.6 ml (157 mmol) pyridine in 230 ml dichloromethane at 0° C. was added dropwise 10.6 ml (137 mmol) methyl chloroformate and stirring continued for 1 hour. The mixture was then poured onto 1 M hydrochloric acid and the organic phase was separated, washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 31.0 g (99%) (4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester as a white solid. ES-MS m/e (%): 239 (M+H+, 100).

Workup

  1. customthe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95294ab135c34daba87c459d9f90d4e2
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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