Benzene → 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,2'-tricyclo(3.3.1.13,7)decane]

HRID 372836

Reaction equation

HRID 372836 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5]([I:13])[C:4]=1[OH:14].C[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[CH:25]1C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:12][C:9]([C:7]1[CH:6]=[C:5]([I:13])[C:4]2[O:14][C:25]3([CH:21]4[CH2:20][CH:19]5[CH2:24][CH:23]([CH2:16][CH:17]3[CH2:18]5)[CH2:22]4)[NH:1][CH2:2][C:3]=2[CH:8]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 241BenzeneHCID 15600DecaneHCID 1192862-Aminomethyl-4-t-butyl-6-iodophenol

Product 1

HCID 128578953,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,2'-tricyclo(3.3.1.13,7)decane]

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol (1.5 g., 0.005 mole), 2-oxotricyclo(3.3.1.1.3,7)-decane (0.75 g., 0.005 mole) and p-toluenesulfonic acid (50 mg.) in benzene (25 ml.) is refluxed under a Dean-Stark trap for 2 hr. The solution is cooled, filtered, and evaporated to dryness. The residue is crystallized from ethanol to obtain 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,2'-tricyclo(3.3.1.13,7)decane] (1.4 g.), m.p. 165°-166° C.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-694f9eba089d4d0da61a765a528ea808
Source dataset
uspto-grants-1978_05
Patent number
US04092414

Linked notes

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