Water → HCID 60055571, compound

HRID 1160995Notes

Reaction equation

HRID 1160995 reaction equation
[C:1](Cl)(Cl)=[S:2].Cl.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][O:17][CH3:18])=[O:15])=[CH:9][CH:8]=1.C(N(CC)CC)C.O>O1CCCC1.C(OCC)C>[N:6]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][O:17][CH3:18])=[O:15])=[CH:9][CH:8]=1)=[C:1]=[S:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 86606887HCID 86606887, compound

Product 1

HCID 60055571HCID 60055571, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Thiophosgene (0.38 ml, 1.1 eq) is added dropwise to a solution cooled down to 0° C., of N-(4-aminophenyl)-N′-methoxyurea hydrochloride (1 g) and triethylamine (3.2 ml, 5 eq) in tetrahydrofuran (90 ml). The mixture is stirred for 15 min at 0° C. then water and diethyl ether are added. After decantation and extractions, the phases organic are combined, washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 7:3 to 3:7) produces the expected compound (630 mg; 62% yield).

Workup

  1. extractionAfter decantation and extractions
  2. washwashed with salt water
  3. dry with materialdried over Na2SO4
  4. concentrationthen concentrated under reduced pressure at 40° C
  5. customPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 7:3 to 3:7)

Sources & evidence

ORD record
ord-b0c52f00667844c9b64f8d5b652e75ab
Source dataset
uspto-grants-2010_10
Patent number
US07816539B2

Reaction notes

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