Triethylamine → HCID 15549378, compound

HRID 1532761Notes

Reaction equation

HRID 1532761 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=1[NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Br:23])=S)[CH:2]=[CH2:3].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=1[N:13]=[C:14]=[N:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Br:23])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15549377HCID 15549377, compound

Product 1

HCID 15549378HCID 15549378, compoundYield 146%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(2-Allyloxy-4-cyanophenyl)-N′-(2-bromophenyl)-thiourea (900 mg, 2.32 mmol) and triethylamine (1 ml, 6.95 mmol) in methylene chloride was added dropwise at 0° methanesulfonyl chloride (360 μL, 4.64 mmol) under Ar. The reaction was stirred for 15 minutes at 0° and tlc showed no starting material present. The reaction mixture was chromatographed on silica gel eluting with methylene chloride to afford the title compound as a yellow solid (1.2 g, >100%). This was used in the next reaction without further purification.

Workup

  1. customThe reaction mixture was chromatographed on silica gel eluting with methylene chloride

Sources & evidence

ORD record
ord-9577e30077a74697867c3ec97ff4edc6
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

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