Sulfuric Acid → HCID 20477980, compound

HRID 904888Notes

Reaction equation

HRID 904888 reaction equation
[CH3:1][C:2]1([CH3:12])[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][CH2:3]1.S(=O)(=O)(O)O.[CH:18](=O)[CH:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1>C1(C)C=CC=CC=1>[CH:19]1([CH:18]([C:10]2[CH:9]=[CH:8][C:6]3[NH:7][C:2]([CH3:1])([CH3:12])[CH2:3][S:4][C:5]=3[CH:11]=2)[C:10]2[CH:9]=[CH:8][C:6]3[NH:7][C:2]([CH3:12])([CH3:1])[CH2:3][S:4][C:5]=3[CH:11]=2)[CH2:24][CH2:23][CH:22]=[CH:21][CH2:20]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 109313902-Cyclohexene-1-carbaldehydeHCID 129047183,3-Dimethyl-3,4-dihydro-2H-1,4-benzothiazine

Product 1

HCID 20477980HCID 20477980, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

90 g (0.5 mole) of 3,3-dimethyl-2,3-dihydro-4H-1,4-benzothiazine, 500 ml of toluene, 3.2 g of concentrated sulphuric acid and 27.5 g (0.25 mole) of tetrahydrobenzaldehyde are refluxed for 5 hours, washed with water, the organic phase dried and the solvent removed in vacuo. Unreacted 3,3-dimethyl-2,3-dihydro-4H-1,4-benzothiazine is distilled off under a high vacuum, leaving as residue 1-cyclohex-3-enyl-1,1-di-(3,3-dimethyl-2,3-dihydro-4H-1,4-benzothiazin-7-yl)-methane in the form of a dark brown brittle resin.

Workup

  1. washwashed with water
  2. customthe organic phase dried
  3. customthe solvent removed in vacuo
  4. distillationUnreacted 3,3-dimethyl-2,3-dihydro-4H-1,4-benzothiazine is distilled off under a high vacuum

Sources & evidence

ORD record
ord-82cbc57cd7034e44895d17156c19baed
Source dataset
uspto-grants-1983_12
Patent number
US04420613

Reaction notes

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