Water → 2-(Methyloxycarbonyl)amino-4-isopropyl-7-methyl-6-thiocyanato-benzothiazole

HRID 1859535Notes

Reaction equation

HRID 1859535 reaction equation
[CH:1]([C:4]1[C:9]2[N:10]=[C:11]([NH2:13])[S:12][C:8]=2[C:7]([CH3:14])=[C:6]([S:15][C:16]#[N:17])[CH:5]=1)([CH3:3])[CH3:2].Cl[C:19]([O:21][CH3:22])=[O:20].O.CCOC(C)=O>C(Cl)Cl.N1C=CC=CC=1>[CH3:22][O:21][C:19]([NH:13][C:11]1[S:12][C:8]2[C:7]([CH3:14])=[C:6]([S:15][C:16]#[N:17])[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9]=2[N:10]=1)=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8857Ethyl AcetateHCID 225729724-Isopropyl-7-methyl-6-thiocyanato-benzothiazol-2-yl-amine

Product 1

HCID 225730782-(Methyloxycarbonyl)amino-4-isopropyl-7-methyl-6-thiocyanato-benzothiazole

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-isopropyl-7-methyl-6-thiocyanato-benzothiazol-2-yl-amine (Example L-4; 4.0 g, 17 mmol) dissolved in CH2Cl2 (25 mL) and pyridine (5 mL), was added methyl chloroformate at 0° C. The reaction mixture was stirred at room temperature for 2 hours. H2O was added to the reaction mixture followed by EtOAc (100 mL). The organic layer was washed with 2N HCl, H2O, saturated sodium bicarbonate solution and brine, and was dried (MgSO4). The solvents were evaporated, and the residue was purified by flash chromatography (100% hexanes to 25% EtOAc in hexanes) to give 2-(methyloxycarbonyl)amino-4-isopropyl-7-methyl-6-thiocyanato-benzothiazole. MS (APCI): 322 (M+H).

Workup

  1. washThe organic layer was washed with 2N HCl, H2O, saturated sodium bicarbonate solution and brine
  2. dry with materialwas dried (MgSO4)
  3. customThe solvents were evaporated
  4. customthe residue was purified by flash chromatography (100% hexanes to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-229ccb15eaa940129ab76bf9425e42b8
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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