4-Nitrophenyl chloroformate → 4-Nitrophenyl 2-methylbenzo[d]thiazol-5-ylcarbamate hydrochloride

HRID 549693Notes

Reaction equation

HRID 549693 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([CH3:12])=[N:9][C:8]=2[CH:13]=1.[Cl:14][C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16]>[OH-].[Na+]>[ClH:14].[CH3:12][C:10]1[S:11][C:7]2[CH:6]=[CH:5][C:4]([NH:3][C:15](=[O:16])[O:17][C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)=[CH:13][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 162189432-Methylbenzothiazol-5-ylamine dihydrochloride

Product 1

HCID 667969364-Nitrophenyl 2-methylbenzo[d]thiazol-5-ylcarbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

5-Amino-2-methylbenzothiazole dihydrochloride (530 mg, 2.23 mmol) was dissolved in 1 N NaOH (10 mL) and was extracted with EtOAc (3×20 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was dissolved in CH2Cl2 (10 mL), p-nitrophenyl chloroformate (586 mg, 2.91 mmol) was added, and the reaction mixture was stirred at rt overnight. The resulting solid was collected by filtration, was washed with CH2Cl2, and was dried under vacuum. This gave 853 mg of the title compound contaminated with some 5-amino-2-methylbenzothiazole. LC-MS: RT=8.49 min, [M+H]+=330.0.

Workup

  1. extractionwas extracted with EtOAc (3×20 mL)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe material was dissolved in CH2Cl2 (10 mL)
  6. filtrationThe resulting solid was collected by filtration
  7. washwas washed with CH2Cl2
  8. customwas dried under vacuum

Sources & evidence

ORD record
ord-15b5a389a63d4b2cab6941ff5ec15742
Source dataset
uspto-grants-2011_05
Patent number
US07943622B2

Reaction notes

Loading…