Triethylamine → HCID 131724302, compound

HRID 1840347Notes

Reaction equation

N=C=N.[Br: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]([NH:25][CH:26]2[CH2:30][CH2:29][O:28][NH:27]2)(=[O:24])=[O:23])[C:16]=1[O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])=S.CS(Cl)(=O)=O.C(N(CC)CC)C>>[Br: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]([NH:25][CH:26]2[CH2:30][CH2:29][O:28][NH:27]2)(=[O:24])=[O:23])[C:16]=1[O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 160435Carbodiimide

HCID 131724298HCID 131724298, compound

Product 1

HCID 131724302HCID 131724302, compoundYield 88.5%

Procedure

Following the general procedure for carbodiimide formation outlined in example 1, N-(2-bromophenyl)-N′-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″-tetrahydroisoxazylaminosulfonyl)phenyl]thiourea (385 mg, 0.74 mmol), methanesulfonyl chloride (0.12 mL, 1.48 mmol) and triethylamine (0.21 mL, 1.48 mmol) were reacted to form the desired product (385 mg, crude). 1H NMR (CDCl3) δ 0.35 (s, 6H), 1.02 (s, 9H), 1.68 (m, 2H), 1.9 (m, 2H), 3.04 (t, 2H), 4.0 (t, 2H), 7.09 (d, 1H), 7.12 (d, 1H), 7.2 (d, 1H), 7.3 (t, 1H), 7.42 (d, 1H), 7.6 (d, 1H).

Workup

customwere reacted

Sources & evidence

ORD record: ord-26dbd4505d5f4a14a09593838475837c
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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