Water → HCID 86688544, compound

HRID 710547Notes

Reaction equation

HRID 710547 reaction equation
ClC(O[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12]1[S:13][C:14]2[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:15]=2[N:16]=1.[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C.[OH2:29].[C:30](#[N:32])C>CC(N(C)C)=O>[Br:21][C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([NH:11][C:22]([N:24]3[CH2:27][CH2:28][C:5](=[CH:10][C:9]4[CH:8]=[CH:7][CH:6]=[CH:30][N:32]=4)[CH2:26][CH2:25]3)=[O:29])[S:13][C:14]=2[CH:20]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8471Triethylamine2×HCID 15891Phenyl chloroformateHCID 851492-Benzothiazolamine, 6-bromo-

Product 1

HCID 86688544HCID 86688544, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

Phenyl chloroformate (3.49 g, 22.3 mmol) was dissolved in acetonitrile (20 mL), and 2-amino-6-bromobenzothiazole (5.06 g, 22.1 mmol) dissolved in dimethylacetamide (20 mL) was added thereto, followed by stirring at 50° C. for 17 hours. The compound (5.51 g, 22.3 mmol) obtained in Example 1 (2) and triethylamine (hereinafter referred to as Et3N) (12.8 mL, 91.9 mmol) were added to the resulting mixture, followed by stirring at 70° C. for 5 hours. Water (120 mL) was added to the resulting mixture, and the precipitate was collected by filtration and washed with ethanol, thereby giving the title compound (5.84 g, 62%) as a brown solid.

Workup

  1. additionwas added
  2. additionwere added to the resulting mixture
  3. stirringby stirring at 70° C. for 5 hours
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-7046813cd971469fbff5cdb9966cb33c
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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