Ammonia → HCID 19001536, compound

HRID 2259647Notes

Reaction equation

HRID 2259647 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([N:11]3[CH2:19][CH2:18][CH:14]([C:15](O)=O)CC3)[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH2:22]([N:24](CC)CC)[CH3:23].C(Cl)(=O)[O:30]CC(C)C.N>O1CCCC1.CN(C)C=O>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([NH:11][C:19](=[O:30])[CH:18]3[CH2:14][CH2:15][NH:24][CH2:22][CH2:23]3)[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 19001522HCID 19001522, compound

Product 1

HCID 19001536HCID 19001536, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

90 g of the N-(6-nitrobenzothiazol-2-yl)isonipecotic acid obtained in the Preparation Example 11 was suspended in 500 ml of tetrahydrofuran and 1,000 ml of dimethylformamide. 100 ml of triethylamine was added to the suspension and 45 ml of isobutyl chlorocarbonate was added dropwise to the suspension under cooling to -20° C. After stirring for 20 min, 100 ml of concentrated aqueous ammonia was added to the mixture at -40° C. and stirred for 20 min. The reaction mixture was poured into ice/water and the formed precipitates were recovered by filtration, washed with water and then with ether, and dried to give 75 g of the titled compound.

Workup

  1. additionwas added dropwise to the suspension
  2. stirringstirred for 20 min
  3. customthe formed precipitates
  4. filtrationwere recovered by filtration
  5. washwashed with water
  6. dry with materialwith ether, and dried

Sources & evidence

ORD record
ord-daf0d2cb7a8749c497599f835dbf98aa
Source dataset
uspto-grants-1995_12
Patent number
US05475014

Reaction notes

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