Benzylamine → HCID 53828591, compound

HRID 1279204Notes

Reaction equation

HRID 1279204 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[CH:3][CH:2]1[C:11]([OH:13])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O=S1(=O)C2C=CC=CC=2N=CC1C(O)=O>CN(C=O)C.C(OC(=O)C)C>[CH2:26]([NH:33][C:11]([CH:2]1[CH:3]=[N:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:1]1)=[O:13])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 53997871HCID 53997871, compoundHCID 54077669HCID 54077669, compound

Product 1

HCID 53828591HCID 53828591, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1,4-benzothiazine-2-carboxlic acid (70 mg, 0.36 mmol) and 1,1′-carbonyldiimidazole (70 mg, 0.43 mmole) in DMF ( 5 mL) is stirred at 80° C. for 30 mins. It is then treated with benzylamine (0.05 mL, 0.43 mmol) and heated at 80° C. for 1 h. The reaction mixture is cooled to room temperature, taken up with ethylacetate, and extracted with water (3×10 mL). The organic layer is dried over sodium sulfate and concentrated. The solid is filtered and washed with ethylacetate to give N-benzyl-1,4-benzothiazine-2-carboxamide (35 mg, 35% yield) as a white solid (compound 1), m.p. 160-162° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionextracted with water (3×10 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated
  5. filtrationThe solid is filtered
  6. washwashed with ethylacetate

Sources & evidence

ORD record
ord-4a274b769ce34dacba7987e01f943333
Source dataset
uspto-grants-2002_09
Patent number
US06448246B1

Reaction notes

Loading…