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

HRID 70156Notes

Reaction equation

HRID 70156 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-38ab128a05964abd866f2b2fa3265fba
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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