Methyl chloroformate → Methyl (7-oxo-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate

HRID 222607

Reaction equation

HRID 222607 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[S:8][C:9]2[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=1>N1C=CC=CC=1.C(OCC)(=O)C>[O:16]=[C:15]1[C:9]2[S:8][C:7]([NH:6][C:2](=[O:3])[O:4][CH3:5])=[N:11][C:10]=2[CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

Product 1

HCID 59703189Methyl (7-oxo-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

572 μl of methyl chloroformate (7.3 mmol) are added to a solution of 500 mg of 2-amino-5,6-dihydro-4H-benzothiazol-7-one (2.4 mmol) in 5 ml of pyridine. The reaction mixture is stirred at 50° C. for 15 h and then diluted with ethyl acetate; the mixture is then extracted by shaking, in each case 2×, with water and cold 1 N hydrochloric acid. The organic phase is dried and evaporated. Yield: 290 mg

Workup

  1. extractionthe mixture is then extracted
  2. stirringby shaking, in each case 2×, with water and cold 1 N hydrochloric acid
  3. customThe organic phase is dried
  4. customevaporated

Sources & evidence

ORD record
ord-c55ba04fda9c408b8eb124b51a903ab9
Source dataset
uspto-grants-2012_06
Patent number
US08207349B2

Linked notes

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