Triethylamine → HCID 23447819, compound

HRID 1840367Notes

Reaction equation

N=C=N.[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[C:16]=1[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=S.CS(Cl)(=O)=O.C(N(CC)CC)C>>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]=[N:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[C:16]=1[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 160435Carbodiimide

HCID 23447742HCID 23447742, compound

Product 1

HCID 23447819HCID 23447819, compoundYield 104.8%

Procedure

Following the general procedure for carbodiimide formation outlined in example 12, N-(2-fluorophenyl)-N′-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]thiourea (357 mg, 0.69 mmol), methanesulfonyl chloride (0.12 mL, 1.38 mmol) and triethylamine (0.2 mL, 1.38 mmol) were reacted to form the desired product (350 mg, crude). 1H NMR (CDCl3) δ 0.38 (s, 6H), 1.05 (s, 9H), 1.72 (m, 4H), 2.87 (s, 6H), 7.06 (d, 1H), 7.19 (m, 3H), 7.28 (d, 1H), 7.31 (d, 1H).

Workup

customwere reacted

Sources & evidence

ORD record: ord-cc19a0196a5347919977f59ee7d270af
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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