Water → HCID 67065159, compound

HRID 2176723Notes

Reaction equation

HRID 2176723 reaction equation
[CH2:1]([CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:12](Cl)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:27][C:28]1[CH:29]=[C:30]([C:38]([O:40][CH3:41])=[O:39])[CH:31]=[C:32]([CH:37]=1)[C:33]([O:35][CH3:36])=[O:34].C(N(CC)CC)C.O>O1CCCC1>[CH2:1]([CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:12]([NH:27][C:28]1[CH:37]=[C:32]([C:33]([O:35][CH3:36])=[O:34])[CH:31]=[C:30]([CH:29]=1)[C:38]([O:40][CH3:41])=[O:39])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66831Dimethyl 5-aminoisophthalateHCID 539445462-Decyltetradecanoyl chloride

Product 1

HCID 67065159HCID 67065159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-decyltetradecanoyl chloride from Step 1 in dry tetrahydrofuran (80 mL) was added dropwise slowly to a suspension of dimethyl 5-aminoisophthalate (Sigma-Aldrich, 4.40 g, 21.0 mmol), triethyl amine (4.4 mL, 31.5 mmol), and dry tetrahydrofuran (100 mL) under an inert atmosphere at 0° C. The reaction was allowed to warm slowly to room temperature and was stirred overnight. Deionized water (10 mL) was added and the tetrahydrofuran was removed by rotary evaporation. The crude residue was then dissolved in 250 mL of ethyl acetate and washed with 3 successive 100 mL portions of deionized water. The ethyl acetate was then removed from the organic phase by rotary evaporation and the product was dried in vacuo to give crude dimethyl 5-(2′-decyltetradecanamido)isophthalate (12.56 g) as a pale yellow solid.

Workup

  1. customthe tetrahydrofuran was removed by rotary evaporation
  2. dissolutionThe crude residue was then dissolved in 250 mL of ethyl acetate
  3. washwashed with 3 successive 100 mL portions of deionized water
  4. customThe ethyl acetate was then removed from the organic phase by rotary evaporation
  5. customthe product was dried in vacuo

Sources & evidence

ORD record
ord-10697a779c07481e9f7aa56afa0d483c
Source dataset
uspto-grants-2015_06
Patent number
US09067878B2

Reaction notes

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