Sodium Carbonate → 4-[N-(carbobenzyloxy)-N-hexadecylamino]-2-thiophenecarbonyl chloride

HRID 850979Notes

Reaction equation

HRID 850979 reaction equation
[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([OH:25])=O)[S:21][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].[C:32](Cl)([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].S(Cl)([Cl:45])=O>C1(C)C=CC=CC=1.O.C(Cl)(Cl)Cl>[C:32]([N:17]([C:18]1[CH:19]=[C:20]([C:23]([Cl:45])=[O:25])[S:21][CH:22]=1)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 24386Thionyl ChlorideHCID 131349944-Hexadecylamino-2-thiophenecarboxylic acid

Product 1

HCID 205036214-[N-(carbobenzyloxy)-N-hexadecylamino]-2-thiophenecarbonyl chloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To 15 g. 4-(hexadecylamino)-2-thiophenecarboxylic acid in 200 ml. warm chloroform is added a solution of 15 g. of sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. carbobenzyloxy chloride. After 2 hours stirring at 40° C., the organic layer is separated, washed three times with 1 N hydrochloric acid, dried, and evaporated to yield an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. thionyl chloride and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time, ultimately to yield 4-[N-(carbobenzyloxy)-N-(hexadecyl)amino]-2-thiophenecarbonyl chloride as a viscous, orange oil.

Workup

  1. additionTo the vigorously stirred solution is added 10 g
  2. customthe organic layer is separated
  3. washwashed three times with 1 N hydrochloric acid
  4. customdried
  5. customevaporated
  6. customto yield an oil
  7. dissolutionThe oil is dissolved in 300 ml
  8. customThe solvents are evaporated
  9. dissolutionthe residue is dissolved three times in toluene
  10. customevaporating each time

Sources & evidence

ORD record
ord-dee7ef99500644879014b8babe03b241
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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