2-Amino-1-(thiophen-2-yl)ethan-1-ol → alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-amino-methyl]-2-thiophen-methanol

HRID 1462369Notes

Reaction equation

HRID 1462369 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[OH:4].CC1(C)[NH:16][C:15](=[O:17])[C:14]2[CH:18]=[C:19]([O:22][CH2:23][CH2:24]Br)[CH:20]=[CH:21][C:13]=2[O:12]1>C(N(CC)CC)C>[C:15]([C:14]1[CH:18]=[C:19]([CH:20]=[CH:21][C:13]=1[OH:12])[O:22][CH2:23][CH2:24][NH:1][CH2:2][CH:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[OH:4])(=[O:17])[NH2:16]

Participants

4

Reactant 2

HCID 4361522-Amino-1-(thiophen-2-yl)ethan-1-olHCID 137544136-(2-Bromoethoxy)-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

Product 1

HCID 20452665alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-amino-methyl]-2-thiophen-methanol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2.7 g of α-(aminomethyl)-2-thiophenmethanol and 3.6 g of 2,3-dihydro-2,2-dimethyl-6-(2-bromoethoxy)-4H-1,3-benzoxazin-4-one is stirred together with 2 ml of triethylamine for 1 hour in a bath at 100°-110°. The reaction mixture is partitioned between 100 ml of ethyl acetate and 10 ml of 2N aqueous potassium bicarbonate solution and the organic phase is separated off, dried over magnesium sulfate and evaporated, yielding crude α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-amino-methyl]-2-thiophen-methanol in the form of a crystalline mass which after recrystallisation from a little isopropanol melts at 158°-161°; repeated recrystallisation raises the melting point to 171°-172°.

Workup

  1. customThe reaction mixture is partitioned between 100 ml of ethyl acetate and 10 ml of 2N aqueous potassium bicarbonate solution
  2. customthe organic phase is separated off
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-01341b80d2994ff1875744b472c8cd27
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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