Water → 1-((4-(Benzyloxy)phenyl)isocyanomethylsulfonyl)4-methylbenzene

HRID 33914Notes

Reaction equation

HRID 33914 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[NH:16][CH:17]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.C(N(CC)CC)C.O>C(COC)OC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N+:16]#[C-:17])[S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=2)(=[O:21])=[O:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 59797510N-((4-(Benzyloxy)phenyl)(tosyl)methyl)formamide

Product 1

HCID 866064171-((4-(Benzyloxy)phenyl)isocyanomethylsulfonyl)4-methylbenzeneYield 107.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of N-((4-(Benzyloxy)phenyl)(tosyl)methyl)formamide (3.2 g, 8.1 mmol) in 43 mL of DME (dimethoxy ethane) at 0° C. was added POCl3 (2.27 mL) followed by the dropwise addition of triethylamine (5.6 mL ). The resultant solution was then stirred at 0° C. for 3 h and finally poured into cooled water. The precipitate was collected and dried to give 3.3 g of pale yellow solid. MS m/z: 378 [M+1]+.

Workup

  1. additionfinally poured
  2. customThe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-b330e53e0c864d3fb81fbecfff6a1f0e
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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