Ammonia → HCID 86656482, compound

HRID 75762Notes

Reaction equation

HRID 75762 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[S:19][C:20]4[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:21]=4[N:22]=3)=[CH:13][CH:12]=2)[CH:7]=1)=O)C.[NH3:28]>>[F:27][C:25]1[CH:24]=[CH:23][C:21]2[N:22]=[C:18]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([C:8]4[CH:7]=[C:6]([C:4]([NH2:28])=[O:3])[O:10][N:9]=4)=[CH:16][CH:15]=3)[S:19][C:20]=2[CH:26]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 665720703-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 86656482HCID 86656482, compoundYield 97.4%

Procedure

A mixture of 3-[4-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carboxylic acid ethyl ester (4.0 g; 10.44 mmol) and saturated methanolic ammonia (250 ml) was stirred to obtain a white solid. The solvent was evaporated, and the residue was stirred with light petroleum and filtered. The residue was washed with light petroleum and dried to obtain 3.6 g (97.4%) of the title compound. Mass (ES+), 355 (M++1); IR (KBr): 3463, 3123 (br), 1700, 1607, 1553 (br); 1447 (br); 1H NMR (DMSO-d6) δ: 7.18 (m, 1H), 7.54 (s, 1H), 7.64 (m, 1H), 7.76 (m, 1H), 7.87-7.90 (br, 4H), 7.98, 8.37(2×br, 2H, NH2).

Workup

  1. customto obtain a white solid
  2. customThe solvent was evaporated
  3. stirringthe residue was stirred with light petroleum
  4. filtrationfiltered
  5. washThe residue was washed with light petroleum
  6. customdried

Sources & evidence

ORD record
ord-341a8025f76a4e69be201527e19afc8c
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

Loading…