Water → (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid phenyl ester

HRID 2220828Notes

Reaction equation

HRID 2220828 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].O>ClCCl.C(O)C.C(OCC)(=O)C>[C:29]1([O:28][C:26](=[O:27])[NH:12][C:10]2[S:11][C:7]3[C:6]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 114028614-Methoxy-7-morpholinobenzo[d]thiazol-2-amine

Product 1

HCID 86601727(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine (26.5 g, 100 mmol) in dichloromethane (56 ml) and pyridine (56 ml, 700 mmol) is added phenyl chloroformate (15.7 ml, 125 mmol) at 0-5° C. and the reaction mixture is warmed to ambient temperature. After 1 h, water (7.2 ml, 400 mmol) was added and the reaction mixture is heated for 1 h to 45° C. Then ethyl acetate (250 ml) and 2M HCL (125 ml) were added and the organic phase separated. After removal of the solvent and recrystallization from tert.butyl-methyl ether and finally from ethanol the title compound was obtained as white solid (80% yield), mp 166-168° C. MS: m/e=386(M+H+).

Workup

  1. temperaturethe reaction mixture is heated for 1 h to 45° C
  2. customthe organic phase separated
  3. customAfter removal of the solvent and recrystallization from tert.butyl-methyl ether

Sources & evidence

ORD record
ord-bbcb79177b714f67b070f7de5d2971de
Source dataset
uspto-grants-2008_05
Patent number
US07368446B2

Reaction notes

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