Benzo(d)thiazol-2-amine → HCID 22797769, compound

HRID 2398720Notes

Reaction equation

HRID 2398720 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[N:24]=[C:25]=[S:26])(=[O:3])[CH3:2].[NH2:27][C:28]1[S:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1>C1(C)C(C)=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[NH:24][C:25]([NH:27][C:28]1[S:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1)=[S:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 12899825HCID 12899825, compound

Product 1

HCID 22797769HCID 22797769, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

To 10 ml of anhydrous xylene were added 390 mg (1 mmol) of 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl isothiocyanate and 150 mg (1 mmol) of 2-aminobenzothiazole (MW 150) and the mixture was heated at 110° C. for 40 minutes and allowed to cool to room temperature. Crystals formed were filtered off and recrystallized from methanol to give colourless needles melting between 179° and 181° C. (uncorrected). Yield: 230 mg (42%).

Workup

  1. temperatureto cool to room temperature
  2. customCrystals formed
  3. filtrationwere filtered off
  4. customrecrystallized from methanol
  5. customto give colourless needles
  6. custommelting between 179° and 181° C.

Sources & evidence

ORD record
ord-49cd3573aa79454e8fb40a60d25ca863
Source dataset
uspto-grants-1977_05
Patent number
US04025622

Reaction notes

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