Tert-Butylamine → HCID 13823540, compound

HRID 1906516Notes

Reaction equation

HRID 1906516 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH:13]1[CH2:15][O:14]1)[C:5]([NH2:7])=[O:6].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>S1(CCCC1)(=O)=O>[OH:14][CH:13]([CH2:15][NH:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][O:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([NH2:7])=[O:6])=[CH:3][C:2]=1[I:1]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 13823542HCID 13823542, compound

Product 1

HCID 13823540HCID 13823540, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A solution of 3.75 g (0.01 mole) of 3-iodo-4-(oxiranylmethoxy)benzamide and 10.5 ml (0.1 mole) of t-butylamine in 7 ml of sulfolane was heated at 90° C. in an autoclave. After 2 hr the vessel was cooled and the t-butylamine was evaporated in vacuo. The residue was crystallized from CH2Cl2 /CH3CN to give 4.0 g (100% yield) of 4-[2-hydroxy-3-[(1,1-dimethylethyl)amino]propoxy]-3-iodobenzamide as a white crystalline solid, mp 111°-114° C.

Workup

  1. temperatureAfter 2 hr the vessel was cooled
  2. customthe t-butylamine was evaporated in vacuo
  3. customThe residue was crystallized from CH2Cl2 /CH3CN

Sources & evidence

ORD record
ord-d213b626f782466f9262c23d4d2a10c5
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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