Water → N-(2-aminobenzothiazol-6-yl)-4-trifluoromethoxybenzamide

HRID 2108900Notes

Reaction equation

HRID 2108900 reaction equation
CC(OC([NH:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:11]=2[N:10]=1)=O)(C)C.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.O>N1C=CC=CC=1>[NH2:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]([NH:18][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:23][CH:24]=3)[CH:16]=[CH:17][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 58305681HCID 58305681, compound2×

Product 1

HCID 23132497N-(2-aminobenzothiazol-6-yl)-4-trifluoromethoxybenzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-aminobenzothiazol-2-yl tert-butyl carbamate (Intermediate 4, 0.900 g, 3.39 mmol) in pyridine (8 mL), 4-trifluoromethoxybenzoyl chloride (0.535 mL, 3.39 mmol) was added. After stirring for 2 h at 60° C., the solution was poured into water (100 mL). The resulting precipitate was filtered off, washed with water and dried. The so obtained solid was dissolved in dichloromethane (20 mL) and trifluoroacetic acid (20 mL) was added. After stirring for 3 h at r.t., the volatiles were removed in vacuo and dimethyl-formamide (100 mL) was added to the residue. The solution was neutralised by adding saturated sodium hydrogencarbonate solution. Water (400 mL) was added and the mixture was stirred overnight. The precipitated N-(2-aminobenzothiazol-6-yl)-4-trifluoromethoxy-benzamide was filtered off, washed with water and dried (grey solid, 1.16 g, 3.27 mmol, 84%). LC/ESI-MS: m/z=354 [M+H]+; m/z=352 [M−H]−; Rt=3.20 min.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with water
  3. customdried
  4. dissolutionThe so obtained solid was dissolved in dichloromethane (20 mL)
  5. additiontrifluoroacetic acid (20 mL) was added
  6. stirringAfter stirring for 3 h at r.t.
  7. customthe volatiles were removed in vacuo and dimethyl-formamide (100 mL)
  8. additionwas added to the residue
  9. additionby adding saturated sodium hydrogencarbonate solution
  10. additionWater (400 mL) was added
  11. stirringthe mixture was stirred overnight
  12. filtrationThe precipitated N-(2-aminobenzothiazol-6-yl)-4-trifluoromethoxy-benzamide was filtered off
  13. washwashed with water
  14. customdried (grey solid, 1.16 g, 3.27 mmol, 84%)

Sources & evidence

ORD record
ord-a6f0e2310ef4463780f278cf26d21a50
Source dataset
uspto-grants-2009_04
Patent number
US07514460B2

Reaction notes

Loading…