Methanesulfonic Acid → HCID 22620737, compound

HRID 841023Notes

Reaction equation

HRID 841023 reaction equation
BrBr.[F:3][C:4]([F:17])([F:16])[C:5]1[CH:6]=[CH:7][C:8]2[NH:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:15]=1.[S-:18][C:19]#[N:20].[K+].[CH3:22][S:23]([OH:26])(=[O:25])=[O:24]>C(O)(=O)C.C(OC(C)C)(C)C.C(O)(C)C>[CH3:22][S:23]([OH:26])(=[O:25])=[O:24].[NH:20]=[C:19]1[N:14]2[C:8]3[C:7](=[CH:6][C:5]([C:4]([F:3])([F:16])[F:17])=[CH:15][C:9]=3[CH2:10][CH2:11][CH2:12][CH2:13]2)[S:18]1

Participants

8

Reactant 4

HCID 6395Methanesulfonic AcidHCID 24408BromineHCID 516872Potassium thiocyanateHCID 16244470HCID 16244470, compound

Product 1

HCID 22620737HCID 22620737, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 3776IsopropanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

The procedure is carried out as in Example 1, but starting with 2.38 g of bromine in 5 ml of acetic acid, 3.2 g of 7-trifluoromethyl-2,3,4,5-tetrahydro-1H-[1]benzazepine and 5 g of potassium thiocyanate in 35 ml of acetic acid. The brown-yellow oil isolated is chromatographed on a silica gel, eluting with ethyl acetate. A yellow oil is obtained which is dissolved in 15 ml of isopropyl ether to which there is added 1 ml of a 1.94 N solution of methanesulphonic acid in isopropanol. The white precipitate formed is filtered off and then dried under vacuum (70 Pa) at 50° C. 0.7 g of 2-imino-9-trifluoromethyl-4,5,6,7-tetrahydro-2H-thiazolo[5,4,3-jk][1]benzazepine methanesulphonate is thus obtained in the form of a white solid melting at 226° C. [analysis C13H15F3N2O3S, % calculated C 42.38, H: 4.1, F: 15.2, N: 7.5, O: 13.3, S: 17.41, % found C: 42.4, H: 3.9, F: 15.2, N: 7.5, S: 17.4].

Workup

  1. customThe brown-yellow oil isolated
  2. customis chromatographed on a silica gel
  3. washeluting with ethyl acetate
  4. customA yellow oil is obtained which
  5. customThe white precipitate formed
  6. filtrationis filtered off
  7. customdried under vacuum (70 Pa) at 50° C

Sources & evidence

ORD record
ord-b8797b8248474cfd9b30056cdc42d67d
Source dataset
uspto-grants-2002_04
Patent number
US06369221B1

Reaction notes

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