Triethylamine → HCID 131724303, compound

HRID 1840348Notes

Reaction equation

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

Participants

Reactant 4

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 160435Carbodiimide

HCID 131724300HCID 131724300, compound

Product 1

HCID 131724303HCID 131724303, compoundYield 105.5%

Procedure

Following the general procedure for carbodiimide formation outlined in example 1, N-(2,3-dichlorophenyl)-N′-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″-tetrahydroisoxazylaminosulfonyl)phenyl]thiourea (547 mg, 0.897 mmol), methanesulfonyl chloride (0.14 mL, 1.79 mmol) and triethylamine (0.25 mL, 1.79 mmol) were reacted to form the desired product (547 mg, crude). 1H NMR (CDCl3) δ 0.36 (s, 6H), 1.03 (s, 9H), 1.68 (m, 2H), 1.9 (m, 2H), 3.53 (t, 2H), 4.0 (t, 2H), 7.11 (m, 2H), 7.14 (t, 1H), 7.2 (d, 1H), 7.3 (d, 1H), 7.39 (d, 1H).

Workup

customwere reacted

Sources & evidence

ORD record: ord-d42a573879814cc4802b67dff0e0ecaf
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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